


Take A Chance

by broadway_babe_literati, PrincessaKyla



Series: Mafia Babes [1]
Category: Gilmore Girls
Genre: Abuse, Adventure, Alternate Universe, Alternate Universe - Canon Divergence, Blood, Drama, F/M, First Meetings, Fluff, Gun Violence, Guns, I Will Go Down With This Ship, Lies, Meet-Cute, Minor Character Death, Past Abuse, Romance, Secret Relationship, Secrets, Sexual Content, brief crossover mention
Language: English
Status: In-Progress
Published: 2015-04-30
Updated: 2016-04-24
Packaged: 2018-03-26 10:34:41
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 12
Words: 61,177
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3847690
Author URL: https://archiveofourown.org/users/broadway_babe_literati/pseuds/broadway_babe_literati, https://archiveofourown.org/users/PrincessaKyla/pseuds/PrincessaKyla
Summary: <blockquote class="userstuff">
              <p>Rory Gilmore meets Jess Mariano while in New York for a field trip. They instantly click, but how will things work with them living in different cities?</p>
            </blockquote>





	1. Hello New York

**Author's Note:**

> This is a prequel of sorts to a Mafia au PrincessaKyla and I are working on. The story takes place around when Rory went to see Jess in New York, except they hadn't met previously. At the start of the story, Rory is still with Dean. Jess lives with Jimmy, Liz was the one that bailed.

Rory Gilmore stepped off the pristine chartered bus along with the rest of her Chilton classmates into the chilly New York air. They were on a field trip to see Phantom of The Opera at the Majestic theatre and then write an essay comparing and contrasting it with that of the book. She watched her classmates group off and get their tickets; she of course, was left by herself so she was given the “odd-ticket-out.”

Her seat was located away from the rest of her classmates. Rory sighed and headed inside to find her seat. The theatre was a pretty big place, she’d done her research on it before leaving on the field trip. Her seat was the only one up in the rear mezzanine section, thus she had to walk up about 3 or 4 flights of stairs. She began her trek after grabbing a playbill. Halfway up the first set of stairs she ran into someone, having not been paying attention in favor of looking through the playbill. She ended up half sitting on a step. “Sorry!” Rory embarrassedly said. 

“It’s alright.” The person said in just-barely-there New York accent, somewhat amused. They offered a hand and helped her up. “Jess Mariano. And you are…?”  
Rory blushed and took his hand.“Rory Gilmore.” She replied shyly. He was gorgeous, to put it bluntly. He had messy black hair, brown eyes and was dressed in dark wash jeans, a Distillers tshirt and leather jacket.

“Well, it’s been a pleasure Rory. Enjoy the show.” He smirked and walked down the steps.

Rory watched him walk away before resuming her trek up the stairs. She then quickly headed to her seat. Once seated she calmed down a bit, but Jess was still at the back of her mind. It bothered her a bit, she shouldn’t be thinking about another guy when she had Dean! Rory dispelled those thoughts and checked her watch, 10 minutes until show time, with that she pulled out her book, Howl & Other Poems by Allen Ginsberg. 

A few minutes later Jess Mariano sat down next to her. “Now who could have known, we’d end up sitting next to each other?” He said partially sarcastically, partially playfully.

Rory looked up in surprise, too shocked to really respond. She laid her book on her lap. 

Jess continued on. “So clearly you aren’t from around here, by the looks of it, some prep school?”

Rory nodded, finally finding her voice. “Chilton Preparatory School in Hartford, Connecticut. What about you?”

Jess shook his head. “I’m not here with a school.”

“Wait, so you’re skipping?!”

“I’m not missing anything I don’t already know.”

Rory gave him a look but didn’t say anything.

A few minutes passed before Jess spoke again, Rory had taken to looking anywhere but at Jess. “So, Rory. Wanna get out of here?”

“What?! No! I can’t leave!” her heart sped up just a bit. 

“Come on, you mean to tell me you’d rather sit here than get out and explore the city?”

He had a point. She’d much rather go explore the city with him. ‘Wait! No! Bad Rory! What about Dean?’ she thought. Rory was quiet a moment too long and her extended silence seemed to be all Jess needed. He took her hand and pulled her up, pocketing her book as well and leading her out to the stairs.

“Jess! I can’t just ditch!” ‘Can I?’ She thought almost helplessly. 

Jess stopped, halfway down the 1st staircase and looked up at her with those gorgeous coffee colored eyes. “Rory. How often do you get a chance like this? Come on, it’ll be fun! And I promise we’ll be back before the show’s over. No one will notice.”

Rory thought for a moment and then smiled, something about Jess sent her heart racing and gave her butterflies unlike anything she’d ever felt with Dean. “Okay, lead the way!”

Jess beamed and led her down the rest of the stairs, through the lobby, out of the Majestic Theatre and they began their way down 44th street. Rory couldn’t be more excited.


	2. Mary, Maggy, Rory

For two and a half hours, Jess had shown Rory his part of the city. He had taken her to a pretty kickass record shop where she ended up getting a GoGos record for her mom, that just so happened to be signed by Belinda. They’d walked through Washington Square park and got hotdogs before catching the subway back to the theatre. And now, he was depositing her back at the theater in time to make it look like she had been there the whole time. How she was going to do her paper, she wasn’t sure, but it had been so worth it.

“And this is where I leave you,” Jess said with a grin. Rory felt her smile drop.

“I don’t want this to be over,” she said quietly.

“Ah but you gotta be on that bus or there might be problems.”

Rory nodded sadly. “Hey,” Jess said, tapping the underside of her chin to make her look up at him. “Give me your hand.”

Confused, Rory did as he asked and offered up her hand. Quickly, Jess whipped out a felt tip pen and wrote a series of numbers on her hand. Not just any numbers, but a phone number. Then he offered her the pen and his hand. “Phone number.” Shyly, Rory wrote her cell number on his arm.

With a grin, Jess kissed her cheek. “Catch ya later, booktease.” With some swagger to his step, Jess headed on his way and Rory floated into the theater to wait until people started to leave. A few minutes later, as people streamed out of the theater, Rory, still in a daze, headed towards the designated meeting spot to wait for the bus. The group gathered around, voices raised in excited discussion. Rory looked distractedly for her book to keep anyone from trying to talk to her about the show and realized -- Jess had never given it back. Even now, it was riding in his pocket further and further away from her. 

Tristan, spotting Rory made a beeline for her. “Hey, Mary. Where’d you sneak off to during the show?” He was about to wait for a response when he noticed the number and name written on her hand. “Well well. What’s this?” he grabbed her hand for a better look. “Jess Mariano?”

Rory snatched her hand back. “That’s none of your business. And I don’t know what you were talking about. I was in the theater, in my seat, the whole time.”

“Really? Cause that record peaking out of your bag says otherwise, Mary.” He smirked. “Or Should I say, Maggy.” With that, he walked away. 

Rory gasped and rushed to hide the record in question. But before she could get very far, Paris grabbed her hand. “Well well well. What have we here? Breaking the rules?” Paris’ snotty voice sounded very high and mighty.

“It’s been there since before we even got on the bus at the school, Paris. My friend Lane gave it to me at the bus stop this morning and I forgot to stash it in my locker okay? The last thing I’d do is give you and Tristan more ammunition.” Rory wasn’t quite sure where the temper was coming from but she suspected it had something to do with being angry with Paris and Tristan for popping her happy bubble after spending time with Jess. Jess, who even as a fleeting thought in her mind was so intoxicating as to make dealing with Paris bearable somehow.

Paris scoffed. “Because I totally believe that. I’m watching you Gilmore, and you’re gonna write this up for the paper.”

Doing her best not to flinch or strangle the snotty bitch in front of her, Rory smiled. “Fine. I can do that.” In a moment of somewhat self satisfied haughtiness, Paris flounced away back to her lackies and started back to a giggled conversation about some guy who had been sitting near them.

Shortly after that they boarded the bus back to Chilton, Rory settled into her seat and let herself calm down. She discreetly programed Jess’ number into her phone and then got comfortable. It wasn’t long before her thoughts drifted back to Jess. This wasn’t good, she was dating Dean after all….but her and Jess...they clicked. They not only had so much in common, but he made her heart race and he took her breath away. Dean, while a wonderful boyfriend, just didn’t make her feel things like Jess did. Sighing, a bit sadly, she realized what she had to do. 

The ride was oddly nerve wracking without her book but Rory had thought of Jess to tide her over and distract her from the hell she knew was coming when she broke Dean’s heart. 

The bus pulled into Chilton, where their families awaited to take them home. Lorelai was resting up against the jeep with two cups of coffee in her hands. Rory filed out of the bus smiling and walked up to Lorelai.

“Hi Mom,” Rory said in her typical quiet manner. “Thanks for coming to get me.” She took one of the coffee cups from her. 

“Well it was either this or the strip club. Figured this was cheaper,” Lorelai replied with a grin. “How was the trip?”

“It was good.”

“Good? That’s it? Not ‘magical’ or ‘entertaining’ or even ‘educational’? Who are you and what have you done with my daughter?”  
Rory laughed and pushed away the hand Lorelai was attempting to press to her forehead. “Are you sick? Fever? Seriously.”

“Mom I’m fine,” Rory insisted still laughing. “I’m just tired.”

Lorelai chuckled. “Well a bus ride sure will wear ya out. I guess that means we’re headed home?”

Rory nodded and leaned her head against the window. “Please and thank you.” Lorelai and Rory climbed into the jeep and Lorelai started up the car. Rory couldn’t wait to take a nap once home. She rested her eyes for the duration of the car ride.

**Notes for the Chapter:**

> Chapter 3 is being written currently, and will be up soon! Thanks for reading!


	3. Lying Is The Most Fun A Girl Can Have

**Notes for the Chapter:**

> Hey lovelies! Sorry for the wait, things have been crazy. I'm going to be updating back to back chapters of this fic, and for those of you who also read A Gentleman Never Tells, I'll be updating that asap! Also have a few other Kingsman fics in the works. Basically I'm drowning in prompts.

It wasn’t long before they pulled into the driveway of the Crap Shack; Rory yawned and got out of the car, following Lorelai inside. “Oh yea, Mom, here.” Rory handed her the record.

“Where’d you get this?” Lorelai asked as she looked it over. “I mean, the GoGos on vinyl is wonderful but I somehow doubt they were selling this at the Majestic.”

“We had about 20 minutes before the show so I went in this record store nearby to pass the time and saw it was signed by Belinda, so I got it for you.” Rory beamed.

Reaching out to take it, Lorelai was about to turn away when she caught a flash of black ink on her daughter’s hand. “What is that?” she asked, still slightly suspicious.

“What?” Rory asked, suddenly sort of jumpy.

Quickly, Lorelai grabbed Rory’s hand and looked over the number penned there. “Aha! You got someone’s number. What’s his name? Is he cute? Cuter than Dean?”

Rory blushed a bit and quickly answered. “It’s not like that at all! He’s the guy that owns the record store; he said to call if I was interested in anymore signed records!”

Lorelai grinned knowingly. “Whatever you say kiddo.”

Rory hmpfed and went off to her room. “I’m taking a nap!”

“Alright. Go dream of your new cutie -- I mean record store owner guy.”

Rory slammed her door in response and flopped on the bed. She took out her phone and saw one new text from Jess.

[Let me know when you get home. -J]

Rory grinned and rolled onto her side. [Home safe and sound. How’s my book? -R]

[ ;) Being acquainted with my notes.-J] Jess actually blushed a bit. He never used emoticons.

Rory stiffened. [Your notes? -R]

[Breathe. I promise you’ll enjoy them, lighten up. -J]

For a second, Rory wondered how he knew she was tense about it, but then she remembered the ease with which they had sunk into friendly banter and light flirting. Even though they’d only known each other a few hours, it felt like years. [I’ll try. Just no pen please? That paper’s really thin. -R]

[What kind of a person do you take me for? I’d never use pen in a book. -J]

[Just making sure. My own mother did that to me once. I still haven’t forgiven her for the ink stain on page five of Alice’s Adventures in Wonderland. -R]

[That pains me and it’s not even my book. -J]

[Exactly. So you can see why I’m protective of books that leave my possession. -R]

[It wanted to come stay with me, needed a change of scenery. -J]

[But just this morning it told me it was happy to stay by my side always! -R]

[But then it met me, couldn’t resist. -J]

[You /are/ fairly irresistible. -R]

[In a purely platonic way. -R]

[Because it would be creepy of me to imply otherwise. -R]

[Uh huh, sure Rory. I know what you’re really thinking. -J] Jess grinned as he reread her previous text.

[Not creepy at all by the way, you aren’t even capable of it. -J]

[Oh /do you now/? *snorts* you clearly haven’t met me. -R]

 

[I do, you think I’m “irresistible.” And, I have too met you, got you to ditch and everything. I’d say I know you pretty well. -J] 

[Oh really? Well then what’s my favorite book? -R]

[Well you had a copy of The Fountainhead in your bag; it was clearly well loved, why? I’ll never know. Ayn Rand was a political nut. -J]

[You have very good deductive reasoning, good sir. And political nut or not, it’s a good book. -R]

[Zzzzzzzz -J]

[Well if you’re so knowledgeable, what’s /your/ favorite book? -R] Despite her best attempts not to be, Rory was giddy with anticipation.

[The Sun Also Rises by Ernest Hemingway. But to be honest, I have a lot of favorites, specifically Howl, anything by the beats and the lost generation. I have a soft spot for Oliver Twist...Salinger… -J]

Rory thought that over for a second. [Hemingway? Really? I mean, Oliver Twist, Salinger, Howl, anything but Hemingway. He’s so boring! -R]

[Now you know how I feel about Rand. Anyway, I have to go, Jimmy is home. Talk later? -J]

[Sure :) bye! -R]

[Bye Booktease. :) -J]

Rory set her phone down and flailed a bit, all giddy and smiling from her chat with Jess. She even felt pretty energized. But she tensed thinking about what she had to do next. She quickly changed into jeans and a nice long sleeve blue sweater. She pocketed her phone and left her room. “Mom?”

“Yes Loin Fruit?” Lorelai called from the living room. “Did you power nap?”

Rory nodded, smiling a bit. “Is it okay if I go out? I wanna see Lane.”

“Don’t see why not. Just don’t do anything I wouldn’t do. Oh. Wait. Don’t do several things I would do, namely getting pregnant and sneaking alcohol.”

Rory rolled her eyes. “Bye mom.” With that she quickly left the house and headed to Lane’s, she needed to talk to someone. And she told Lane everything. It was weird not being able to talk to Lorelai about this. Oh well. She thought.

About five minutes later she was letting herself into the shop. “Lane?”

“Rory?” Lane called, her voice muffled by the intervening stacks of furniture.

“Uh...how about you come to the front? It’ll take me ages to follow your voice.”

Lane sighed loudly. “Give me a second. A stack of chairs shifted, trapping me.”

“Okay.” Rory giggled.

There was the sound of wood sliding against wood, a groan of frustration and then a shout of victory. “Free! Be there in two seconds.” Within a minute, Lane had made her way to front of the store. “Ta-daa!”

Rory whispered her next words. “I really need to talk to you, can we go somewhere?”

Lane looked her over for a second and then called out, “Mom, Rory and I are going to Luke’s for coffee. I’ll be back in an hour!” Quickly, she ushered her friend out the door. “Quick before she has time to respond or ask questions.”

They quickly hurried out the door. “I was thinking we could go to the bridge? No one will overhear…”

“That bad huh?” Lane asked, hooking her arm through her friend’s. “Well, if Mom asks any questions, Luke’s was really crowded when we got there and we decided to take a walk instead.”

Rory smiled, relieved and headed to the bridge. It was a rather short walk. Rory sat down and let her legs dangle over the side. “I think I’m cheating on Dean!” she blurted out.

Lane plopped down next to her. “Woah stop the presses. Start from the beginning. I’m good but not that good.”

“Okay...well, I met this guy, Jess, in New York today, at the Majestic theatre. And just...just instantly he took my breath away. But then we ended up sitting next to each other and then one thing led to another and I ended up ditching the show and he showed me around the city! Lane it was so amazing!! We went to Washington Square Park, had hot dogs, took the subway, and went to a record store! And...and he kissed my cheek! And before I left we exchanged numbers. But Lane we have so much in common! I spent an hour texting him about books before I came over.” Rory finally stopped, needing to breathe. 

Lane let out a quiet “wow” and turned to look at Rory, clearly excited. “But what about Dean?” Lane asked, suddenly serious.

Rory bit her lip and fiddled with her sleeves. “I don’t love him...I don’t..I don’t really feel anything besides friendship. I think it’s been that way for a while. Jess... Jess makes me feel things. And I...” Rory took a deep breath. “I’m going to break up with Dean.”

Lane nodded. “Can’t say I blame you. This Jess guy sounds amazing. What are you gonna tell Dean? And what about your mom?”

“I’m going to be as honest as I can be. But Jess is a secret, Lane. You have to promise, my mom, /no one/ can find out.” Rory held out a pinky.

Lane hooked her pinky with Rory’s and squeezed. “Promise. But why? I mean I get that breaking up with one person for someone else is bad but what about your mom? You never keep secrets from her.”

Rory shook her head. “She’d never let me see him again, certainly wouldn’t let me go to New York. And she would kill me if she found out I skipped the show to run around New York City with a guy I just met. Lane I cannot tell her.” 

“Alright. She’ll get not a peep from me,” Lane swore.

Rory hugged her before standing. “I need to go break up with Dean now...”

Lane hugged her back. “Good luck, girlfriend. Let me know how it goes?”

“I’ll call you later.”

With that, Rory quickly headed to Dean’s house. She wasted no time ringing the bell once there.  
Anxiously, she fidgeted with the sleeves of her sweater. When Dean answered the door, she burst out with, “I need to talk to you.” 

Dean blinked, a bit shocked by the outburst. “Okay...uh...here?” Dean closed the front door behind him. 

For a few seconds, Rory just looked at him. “I...I want to break up,” she finally said, her voice breaking.

Dean actually stumbled back. “What?! Why?!” 

She swallowed hard. “I just...I don’t...my feelings for you don’t match your feelings for me, and I really just...I don’t want to tie you down when there’s someone else whose feelings will match yours.” She looked at him, her eyes large. “Please, don’t be mad.”

Dean ran a hand through his hair. “Don’t be mad? What the hell Rory?! How can I not be mad you just….you just do this out of the blue! I thought everything was fine!”

“Please Dean. I really just want you to be happy and if we stay together, you won’t be. Trust me.”

Dean shook his head. “Just go Rory.” His voice broke halfway through the sentence. 

She nodded and turned away. Halfway through her first step she turned around and looked at him. Thoughtlessly, she brushed her hair out of her face with the hand still carrying Jess’ number. “For what it’s worth, I’m sorry.”

“So am I,” he said as he looked up, he noticed the phone number but decided to keep it to himself. Things made much more sense now. He then went inside and shut the door, not caring if it slammed.

Wrapping her arms around herself, Rory started making her way home, passing through town and ignoring several concerned looks on her way.

Luke noticed and called her name from the front of Luke’s. “Rory! Can you come here?” He never made it a point to meddle, but Rory looked so….down. She was a good kid; least he could do was give her some coffee to go. 

“What’s up Luke?” Rory asked dejectedly as she walked up to him.

“Just hold on a sec. I’ll be back.” He quickly filled a to go cup and hurried back. “Here.”

Rory seemed confused as she accepted the cup. “Did Mom call in an order for me to pick up on my way home?”

“No, just. Look, just take it, it’s yours.” He gave her a slightly awkward headpat and went back in the diner.

Still confused, Rory shook her head and continued on her way home, nursing her coffee as she went. Rory made it home a few minutes later, just as her phone buzzed in her pocket. Deciding she would rather get inside before she pulled her phone out, Rory downed the last of her coffee and trudged up the steps and let herself inside. The house was oddly quiet and Rory wondered if her mom was out. Remembering the buzz of her phone, Rory pulled it out of her pocket and sighed.

[Hey. -J]

[Hey -R]

[You okay? -J]

[You want the truth or the party line? -R]

[Truth, I always want the truth Rory. -J]

Rory sighed and leaned against the front door. [I feel like a total piece of shit. -R]

[You want to call me? Vent away, sounds like you need it. -J]

For a second, Rory thought about it. It would be nice to talk about it, but did she really want to discuss this with Jess?

[Rory, come on, I won’t judge. You’re upset clearly, just...I want to help. -J]

As soon as she saw that, Rory hit the button to call Jess. Before he could even get out a hello, the words started tumbling out of her mouth. “I just broke up with my boyfriend because I don’t love him and I feel horrible for hurting him, but I didn’t want to keep seeing him when I didn’t feel anything for him, especially once I realized I kind of have feelings for you and now I just feel like I’m pushing this forward too fast and on my God.”

Jess paused before he spoke. “First, I want you to take a deep breath okay? Maybe a few of them.”

Rory did as he asked, trying her best to calm down enough to talk at a normal, human pace. “Okay.”

“Look, Rory, this thing with us? We can take it as slow or as fast as you want. You’re in charge. If...if you need to take some time till you’re not hurting, okay. I’ll still be here.” Jess took a shaky breath. 

Taking another deep breath, Rory responded quietly, “That’s just the thing. I’m not hurting...I’m mad at myself for hurting Dean but I’m not...I’m not hurt and I thought I would be.”

“Well… what do you want to do? We could work on just getting to know each other for now? Honestly, Rory I’m fine with whatever. As long as you’re okay..” Jess wasn’t the best at relationships, let alone expressing his feelings. 

“I don’t...I don’t know. I want to see you again and I want to get to know you and argue about Hemingway versus Rand because Dean and I could never do that. But at the same time, I feel like I should respect that I just dumped my boyfriend. It’s weird. But I do know that I want to get to know you and I want to see where this goes.”

“We can do all of that, whatever you want. We can text, we can talk on the phone...though I work a lot so I should probably tell you when I work...” Jess trailed off. The verbal thing came and went. 

Rory grinned. “I’d like that. So where do you work?” She pushed off from the front door and headed towards her room.

Jess bit his lip and took a moment before answering. “I work for my dad, he runs a business. I do a lot of grunt work, though honestly everything would fall apart without me. I tend to work a lot of odd hours, nights or early mornings. But since he thinks I need to go to school, I’ve been working weekends and after school. I could take a day off though?” Jess took a few breaths. Geeze, this was the most he’d probably ever said to anyone. 

“Huh. I had you down as more of a...waiter, sells all the little old ladies that come in on the special dessert? What kind of business does your dad run?”

Jess panicked slightly. He certainly couldn’t tell her the truth; yea my dad’s a mafia boss. That’d certainly end well. ‘He’s in uh… finance? Loans, stock, boring crap.” 

Rory nodded. “Sounds appropriately boring for a dad in NYC. I’m gonna guess that you’re good at math, then?”

Jess actually laughed. “No. I can make change and deal with large sums of money but no algebra shit.”

Rory laughed. “Oh come on. Surely a smart guy like you wouldn’t have that much trouble.”

“Rory. They put letters with the numbers. It’s stupid and I hate it. That’s why I read.”

Rory laughed harder. “But it’s so much fun! Maybe not quite as much fun as reading but fun.”

“No.” 

She chuckled. “Okay. Want me to tutor you?”

“Yes.”

“And to be clear, I do mean actually tutor you. Like books and practice problems.”

“Uh huh.” You could practically feel his smirk. 

Rory rolled her eyes and said, “I mean it Jess. Real tutoring.”

Before Jess could answer he heard the front door slam. “JESS GET OUT HERE YOU USELESS PIECE OF SHIT!” Jess flinched; there was no way she hadn’t heard that.

“Rory I have to go. I’m sorry.” just as he was hanging up there was more shouting, another bang and then the line went dead. 

“Jess!? Jess!?” Rory looked at her phone. He was gone. Frantically, she sent a text. [Is everything okay? Are you okay? -R]

It was almost an hour before he responded.

[I’m fine. Everything is fine now. I’m sorry I had to hang up. -J]

[Jess...I don’t mind you hanging up but I just...That didn’t sound like “fine” to me. If you don’t wanna talk about it, that’s fine, but you can always talk to me. -R]

“Fuck…” Jess ran a hand through his hair. [Alright. I’m not fine, but I don’t want to talk about it either. I’m used to it. -J]

Rory sighed. [Okay. But I’m here if you ever do want to talk. -R]

[You’d be the first to know, the only actually. -J]

[Not many people you can talk to huh? -R]

[I don’t talk to people unless necessary. It’s safer to keep my mouth shut. -J]

[New subject. -J]

Somewhat shocked, Rory thought about what to talk about for a second before asking, [So what do you do in your spare time? Besides read.-R]

[Listen to music, hang out in Washington Square Park, and fuck off around the city. -J]

[Okay...I might also sneak into Broadway shows. -J]

[But you don’t know that. -J]

Rory laughed. [You totally sneak into Broadway shows don’t you? What’s your favorite? -R]

[Next To Normal or Spring Awakening. I like most of them though. -J]

[Wow. Dark tastes, huh? -R]

[They’re relatable. -J] That’s all he said and he hoped she wouldn’t press. 

[Just...pick up the soundtracks sometime. That’s me “talking about it.” -J]

[Oh, okay then. Guess that makes sense. I think my friend Lane has those. -R]

[She has good taste. -J]

[Eclectic but good. -R]

[Nothing wrong with eclectic, I don’t exactly give off the Broadway fan vibe. -J]

“ROOOOOOOORRRYYYYYYY, MOMMY IS HOME.”

Rory groaned quietly. [Now it’s my turn to disappear. My mom’s home. Talk to you soon? -R]

[Yea, goodnight. -J]

Before Rory could respond, Lorelai burst into the room, coffee in both hands. “There you are munchkin. Ain’t no hiding from me.”

“I was not hiding!” 

“Uh huh. Generally, when someone calls out that they are home, they do it expecting a response.” She sat on the bed. “Ya know a sort of, call and reply type thing?”

Rory stuck her tongue out. “I was finishing my coffee.” 

Lorelai looked around. “What coffee? I see a notorious lack of coffee cups in your vicinity.”

Rory held up her to go cup that was resting behind her books.

“Ah. I stand corrected. Why did you stop and get coffee without me? Are you having coffee with someone behind my back?” Lorelai feigned hurt.

Rory couldn’t help but laugh. “No, I just stopped by Luke’s on my way home.” 

Eyeing her critically, Lorelai asked, “Was Lane with you?”

“The first time yea, but we ended up leaving because it was too crowded.” 

“Uh huh. Luke’s….crowded at four in the afternoon? Okay, well there is obviously something you don’t want to share so I will let you get back to whatever it is they’re having you kids do for homework these days.”

Rory huffed. “We didn’t go straight to Luke’s but I’m done being interrogated,” with that she pulled out her history homework. 

Lorelai’s head snapped backwards a little at the huffiness but she knew better than to push. Rory would let loose a torrential outpouring of words when she was ready to.

Rory scribbled away in her notebook, outlining the most recent reading assignment. 

Before she could get chewed out again, Lorelai got up and quietly made her way from the room, closing the door behind her. She wasn’t sure what was wrong, but she had a feeling the phone number on her daughter’s hand and the fact that people had seen Dean and Rory fighting might have something to do with her rotten mood.

**Notes for the Chapter:**

> I've created both a Playlist and Pinterest board for this fic :) come visit me on tumblr for those links: broadway-babe-eggsyunwin 
> 
> Thanks for reading!


	4. Walking Disaster

**Notes for the Chapter:**

> This chapter contains somewhat graphic depictions of abuse. Basically, Jimmy takes his anger out on Jess. There is also mention of a hospital visit this all begins at line: 
> 
> "As Rory settled back into the couch, her phone started buzzing. With a glance at the screen, Rory could feel her face light up. Jess. “Hey,” she answered cheerily."
> 
> and ends at 
> 
> "Rory rolled her eyes and waved off her mother’s curious looks. [Saturday. If you’re even allowed to go anywhere. -R]"

After Rory got home from Chilton, she changed into jeans and a pale blue tshirt. She grabbed her phone and her red jacket before she headed to the door. “Mom! I’m going to Lane’s!”

“Alright, just be back before the goblins come out or I may wish you away!” 

Rory giggled as she made her way out and to Lane’s. Though once Rory started into the heart of town, she began to notice all the eyes on her. Some people gave her sympathetic looks, others seemed confused. It took a minute before Rory realized why she was getting so many looks. It had clearly made it around stars hollow that she and Dean had broken up. She quickly hurried to Lane’s house and went right in. Mrs. Kim was currently away at a prayer meet so Lane and Rory could talk all they wanted. “Lane! I’m here!” 

“In the kitchen!”

Rory walked into the kitchen, smiling. “Hi.” 

“Hey!” Lane responded brightly. “Sandwich?”

“Yes, please!” Rory took a seat at the kitchen table.

“Alright, we have turkey, ham, or nutella. And maybe some peanut butter?”

“I would love nutella and peanut butter.” 

“Coming right up.” As Lane got together the stuff for sandwiches, she glanced over at Rory and said, “So how’re you holding up?”

Rory blinked confused before it dawned on her. “Oh! Yea, I’m actually...really good.”

Lane nodded and was quiet for a moment as she finished making Rory’s sandwich. “Has anybody asked you about it yet?”

“No, but I had everyone’s eyes on me as I walked here. I know that I should feel bad or feel something, but I’m honestly just relieved and then...Jess...that has me in a happy mood.” Rory took a bit of her sandwich before she spoke again. “Does that make me a bad person?” 

Lane shook her head. “You feel bad for hurting Dean right? And you did it so you wouldn’t cheat on  
him, right? So I don’t think it makes you a bad person. You don’t love him and you did the right thing.”

Rory immediately felt better. “Jess and I have been flirting a lot.” Rory shyly ate her sandwich, hoping her blush wasn’t too noticeable. 

Lane grinned. “How flirty we talking here?”

“I may have said he was irresistible? And he may have turned tutoring into an innuendo…” 

Lane squealed. “Oh my gosh. Rory! That’s great! But are you sure you aren’t moving too fast?”

Rory nodded. “He made it clear that I was ‘in charge’ we could go as fast or as slow as I wanted. And I’d like to try and visit him soon?” 

Lane looked impressed. “Well he gets points in the best friend book for that. And how soon we talking? Think I’ll be able to tag along?”

“This coming weekend? So...that’s like 4 days away? Also, I’m supposed to ask you to borrow both Spring Awakening and Next To Normal’s soundtracks.” 

Lane thought that over for a few seconds. “I have both upstairs beneath the ever loved floorboards. As for this weekend…Mom’s fairly happy that I aced all my classes this semester so she’s more likely to say yes to going to a show with you. Think your mom would drop us off?”

Rory thought for a moment. “I’m not sure about having my mom drop us off in New York; she’d probably want to stay with us.” Rory bit her lip. “But what if we say we’re going to Hartford? I know the Winston downtown is playing Phantom, and mom would be fine with us hanging around down there during the day before the show? We could take a bus to New York and be back when the show is over.”

Lane blinked. “That’s an amazing plan but remember the last time we lied to your mother so that she wouldn’t be forced to lie to my mother? And that was in town. Only one layer of lying. This is multiple layers.”

Rory was quiet for a moment. “What if Jess met us in Hartford and we really did spend the day there? Then next week I could go to New York so you wouldn’t have to have multiple layers of lies?” 

“Sounds much better. And if Jess is willing to meet us, perfect. We run the slight risk of your grandparents getting involved but that’s probably safer than trying to lie our way to New York.”

Rory beamed. “I’ll call him now!” Rory all but ran upstairs to utilize Lane’s closet hangout. “Lane, come on!” 

Lane laughed. “I’ll be up in a sec. Let me clean up a bit, so Mom doesn’t have my head if she gets home early.”

“Okay!” Rory closed Lane’s door and took up residence in one of the beanbags in Lane’s closet. She took out her phone and called Jess. 

Jess picked up on the third ring. “Hello?” 

“Jess? It’s Rory.”

Jess smiled and tucked his book back in his pocket. “Hey Rory. What’s up?”

“I was wondering if, perhaps, you would be able to meet me and my friend Lane in Hartford on Saturday? Maybe come see Phantom with us that evening?”

Jess though for a moment. “Sure, I can make it. What time? I think the earliest bus is like 8am and I’m about 2 and a half to 3 hours away…” 

“Well the show is at seven or eight, so I was thinking noon? We could meet up and hang out, maybe get ice cream.”

“Sounds good.” 

Rory could hear Lane opening the door and pulling up floorboards to find the CDs Rory had asked to borrow. “So do you have time to talk for a bit or do you need to go?”  
“I have time, I’m just sitting in the park.” 

Rory grinned and when she noticed Lane was opening the closet doors, she quickly motioned her over. “Well, then I would like to introduce you to Lane Kim. Just a sec.” Rory handed the phone to Lane and smiled.

“Hello?” Lane said, slightly thrown by the suddenness.

“Uh..hi, Jess Mariano.” Jess was just as thrown.

“Nice to put a voice to a name,” Lane joked.

“Likewise.” Jess said with a hint of a smirk. 

“Rory tells me you have quite the music taste.” He may as well make an effort to talk, it was for Rory after all. 

“I guess you could say that. Are you the one who recced Next to Normal and Spring Awakening?”

“I am. I told Rory it might help her understand some things. And they’re must haves for any new Broadway fans.” 

Lane nodded. “Point taken. Well now that we’ve put ourselves through the paces? Maybe you’d like to talk to Rory again?”

“That’d be great...nice meeting you Lane.” Jess almost kicked himself. Rory was turning him into a talkative sap. Not that he minded too much…

Lane handed the phone back to Rory and turned to plop down on a beanbag.

“So you two seem like you’ll get on well,” Rory joked.

Jess laughed a bit. “I’m sure we will. I’d introduce you to my “friends” but they’re all dicks, so I’ll spare you.” 

“Sounds like you need better friends then,” Rory said matter-of-factly.

Jess shrugged. “You’re not wrong.” 

“Another thing you don’t wanna discuss?” Rory asked. She wasn’t upset, just clarifying.

“Nah, it’s okay...just maybe not right now. Tell me about your day. What are you and Lane up to?” 

“Oh just hanging out. Dishing on how the day went -- surprisingly well, considering the fact that I broke up with my boyfriend last night. What about you? How was your day?”

“Live in a small town? I Skipped school to see a concert in Brooklyn, then I headed to Washington Square Park to read and then you called.” 

“Skipping school two days in a row? Risky business, mister,” Rory said, feigning disapproval. His willingness to break rules was appealing in a way she never thought it would be.

“Not like they have anything to teach me, I don’t already know. Look, I’ll go tomorrow, okay?” 

“What about Algebra? Surely they can teach you something about that?”

“Thought you were gonna tutor me?” 

“I can only do much. Tutor you I will but don’t expect miracles, Mariano.”

Jess laughed. “Alright Gilmore. I could probably teach you a few things too…” he let himself trail off. 

Rory fought back a blush. “I’m sure I don’t know what you mean.”

“Huh. Cause I’m almost positive you do.” He said with a slight something in his voice. 

Meanwhile Lane had noticed Rory’s blush and was grinning. 

“Oh but I really don’t,” Rory insisted, getting into the groove. “I am a sheltered girl.”

“Guess we’ll have to fix that then. After all, how sheltered can someone be if they follow an ‘irresistible’ stranger around New York.” 

“Very very sheltered, because that is incredibly naive. I mean, for all I knew, you could have been an ax murderer! And I don’t think there’s anything to fix.”

“You could have been an ax murder, I didn’t know you either.” He paused. “You’re right though, there’s nothing to fix.” Jess’ voice was a bit softer. “I’ve got to head to work, text you later, Booktease.” 

“Oh okay. Bye Dodger!” 

“Bye Rory.” Jess hung up, unable to help his smile. 

Rory sank back into her beanbag chair, a silly grin on her face. “He’s perfect…”

Lane grinned and supplied, “Sounds like it.”

Rory giggled a bit. They ended up chatting for another hour or so before Rory had to leave. Mrs. Kim was coming home and she hoped to avoid a run in. 

As she made it out the door and down the front walk, her phone buzzed, indicating she’d received a text. Hoping it was Jess, Rory was somewhat surprised to see that it was Lorelai.

[Hey squirt. Meet me at Luke’s. -L] 

[On my way. -R] It was a short walk to Luke’s. 

As soon as she saw Rory, Lorelai caught her attention with a waving arm and a “Yoohoo!”  
Rory waved and came over. 

Before any questions could be asked, Lorelai pointed at the chair across from her. “Sit. Spill.”  
Rory sighed. “I guess you’ve heard then?” 

“Uh huh. And heard. And heard. But not from you. So what’s going on, Rory?”

Rory bit her lip. “Can we take our coffee home and talk?” 

Lorelai nodded. “If that’ll make this easier, then sure. Luke! We need two to-go cups please?”

“Lorelai this is your third cup!” Rory couldn’t help but smile at their banter. 

“Okay but it is my last cup from you and it is justified by the very serious heart to heart my daughter and I are going to go home and hear about her failure to share about her breakup with her own mother.”

Rory’s jaw dropped and Luke looked a bit shocked too. “Uh...alright...” he went off to get their coffee without another word. 

Mother and Daughter sat and waited in silence. When the coffee arrived Lorelai said, “Thank you Luke. And just to clarify, I meant my last cup from you for the day.”

Luke just shook his head and this left. Rory sipped her coffee as they walked and occasionally glanced at Lorelai. 

Lorelai, for her part, kept her eyes forward as they went, resisting the urge to stop and just force the events of the previous day out of Rory right then and there.

Soon enough they were home, Rory headed inside first. 

Lorelai followed and indicated that Rory should plant herself in the living room. “Alright.”

“Well… we broke up..” Rory took a sip of her coffee as she tried to get her words together. “I just...don’t love him, I don’t feel what he feels for me. And I didn’t want to hurt him and I also didn’t want to keep pretending that I felt more than I did. We just don’t have very much in common. He doesn’t like to read like I do, I don’t like sports..” Rory finally had to take a breath. “I’m really sorry I didn’t tell you.” Her voice was small. “I just needed some time to process. Lane was a nice distraction.” 

Lorelai was slightly taken aback. “Wow kiddo. That’s a lot of word vomit. And don’t apologize. I’m more mad that he seems to have spread it around everywhere than I am that you didn’t tell me, although it is just a bit irksome that you didn’t.”

“I was planning on telling you when I got back from Lane’s but then you texted me about Luke’s” She took another sip of her coffee. “Everyone keeps looking at me..” Her voice wobbled a bit. 

Lorelai gave a sympathetic smile. “I know, but it’s just because you’re the biggest piece of gossip since we found out Rachel invited Luke to her wedding. It’ll blow over eventually I promise.”

Rory got up and sat down on the sofa to cuddle with Lorelai. “Promise?” 

Lorelai wrapped an arm around her daughter and gently pulled her closer. “I promise. I survived it and you will too.”

Rory felt much better. “Movie?” she looked up, hopeful.

“Sure, kiddo.” Lorelai dropped a kiss on top of her head. “Want me to go get snacks and rent something?”

“Yes please!” Rory beamed. 

“Alright. Are we going chick flick, adventure, comedy? Off-the-wall indie?”

“Hmm. Comedy, please.” 

“Comedy it is. And I’m assuming we need a mound of candy?”

“Of course! And lots of soda!” 

“Noted.” Lorelai grabbed her purse and was halfway to the door before thinking to ask, “And if I see Dean?”

“Don’t engage.”

“Right. Okay, I am gone and will be back momentarily.” With a grin, Lorelai was out the door and headed into town.

As Rory settled back into the couch, her phone started buzzing. With a glance at the screen, Rory could feel her face light up. Jess. “Hey,” she answered cheerily.

However she wasn’t greeted with a response. There was some clanging and what sounded like a door slamming shut. “JESS! GET OUT HERE.” Footsteps loudly approached and a muffled, slightly panicky “Fuck” was all Jess said. 

“Jess?”

The voice got closer and louder as did the footsteps. “Jess you really fucked up this time! Can’t you do anything right?!” Jimmy Mariano pulled his fist back and punched Jess right in the face. Jess stumbled back and hit the wall. “What, cat got your tongue? I asked you a question! Answer me!” Jimmy brought his knee up into Jess’s ribs. Jess failed quite miserably at containing his cry of pain. Jimmy did it again, when he didn’t get a response. 

Jess coughed and wheezed. “It w-wasn’t my fault! Defranco was supposed to be handling it!”

“And who’s in charge of Defranco? You are!” Jimmy threw him into the wall again before he stormed out. 

Rory sat in silent horror. While she wasn’t 100% sure, she was fairly certain, based on the noises and yelling she’d heard, that Jess had just been beaten up. And she had the sneaking suspicion it had been his father delivering the beating. “Jess?” she asked timidly.

Jess heard Rory say his name and his blood ran cold as he finally noticed his phone lit up on the bed. He crawled over to the bed and hastily wiped his tears. When he answered, his voice was rough. “Rory?” 

“Oh my God, Jess are you okay? Please please tell me you’re okay.” Rory found her relief at just hearing his voice overwhelming, but she was still worried about him.

“You weren’t supposed to hear any of that…” His voice wavered, almost like he was on the verge of crying. 

“I figured as much but that just makes me even more worried. Are you okay? Talk to me, please.”

Jess took a few shaky breaths. “I think I’ve got a few broken ribs… definitely bruises, black eye... ” 

Rory squinched her eyes shut. “Is there anyone who can take you to the doctor? You need to make sure none of those broken ribs punctured anything. Make sure there’s not serious internal bleeding.”

Jess laughed. Not a haha laugh, but a slightly hysterical one. “Rory, no one gives two shits about me. My mom ran off when I was born, you heard my Dad, and the only other family I know of is my mom’s brother who lives god knows where. I’ll take myself to the E.R like I always do.” 

Rory took a deep breath. “Just be careful. What are you gonna tell them?”

“They don’t ask questions by now, my answers are always the same.” 

Rory nodded, despite knowing he couldn’t see her. “Jess, you can’t stay there, not if he’s going to treat you like that. There has to be somewhere you can go.”

“Rory, you don’t just leave the Mariano family. Someone will always drag you back. Look, I’ll just spend the night in my car.” 

“What like the mob? Jess that’s not healthy or safe.”

“New subject.” Jess said almost desperately. 

Rory paused. “Jess? Are you okay?” Something in his voice had her on edge. Something that had crept in when she brought up the mob.

“I’ll be fine.” He stood up and let out a hiss of pain. He grabbed his bag and shoved some things in it. 

“Jess, scale of one to ten how bad’s the pain when you move?”

“...6? 7? I don’t know, I’ve had worse.” 

“Does it hurt to take a deep breath?”

Jess paused to find out and made a choked noise. “I’d say yes.” he wheezed out. 

Rory thought. “How close is the nearest E.R.?”

“Four blocks.”

Rory considered. “Be careful okay? I…” Rory bit her lip. She had almost said, ‘I love you,’ but right now might not be the best time to make that revelation.

Jess felt a tug at his heart when Rory has started to say what he assumed was either ‘I love you.’ or ‘I care about you.’ He wasn’t used to that, “I never leave unarmed. I’ll be fine. I’ll even text you when I get there.” 

“You better. I’m going to give you forty-five minutes before I start panicking.”

Jess was already walking down the hall outside his apartment, he smiled at her words. “I promise I’ll text you before then. I gotta go now though. Don’t...don’t worry, okay?” 

“I’ll do my best but asking someone who cares about you not to worry is a big request.”

Jess felt that tug at his heart again, he paused for a moment. “I care about you too, I’ll text you soon. Bye Rory.” 

“Bye Jess.” Rory hung up the phone, trying her hardest to smooth the worry from her face.

Lorelai arrived back home about 5 or so minutes later, bundled down with snacks and movies. 

“So,” Lorelai said, dumping her haul onto the coffee table. “I have...red vines, chocolate galore, cheddar cheese puffcorn and some orange Starkist. I also.” She grabbed the movies. “Have Bring It On, Bridget Jones’s Diary, Hedwig and The Angry Itch…”

“I vote we start with Bridget Jones’s Diary because Colin Firth is gorgeous…and Hugh Grant to be honest; then follow up with Bring It On, Then Hedwig.” Rory grabbed the cheesy puffcorn. 

“A very good selection, m’dear,” Lorelai said, moving to pop the movie in.

Rory got comfy and arranged her snacks. 

As the movie got started, Lorelai moved towards the kitchen. “Coffee?”

“Yes please!” 

Lorelai smiled and moved away to make the coffee. As she moved loudly about the kitchen, Rory felt her phone buzz.

[At hospital, checked in. -J]

[-attachment- -J] It was a frowning Jess sitting on a E.R bed, with an IV in his arm. 

[Good. Aw poor baby. Want me to kiss it better? -R]

[ ;) yes please. -J]

Rory fought to restrain a giggle. [Not like that, you perv. :P -R] Then it hit Rory. [Wow you got seen fast. Normally it takes forever. Are they not crowded? -R]

[Got priority as a regular. -J]

[..and I may have… Passed out in the entrance.. -J]

Rory stiffened and fought to relax as she heard her mother heading her way. [Oh my god are you okay? -R]

[Well, I’ve got a morphine drip, and I believe you promised a kiss so.. -J]

Rory rolled her eyes and waved off her mother’s curious looks. [Saturday. If you’re even allowed to go anywhere. -R]

[I’ll be there. It’d take a lot more than this to keep me away. -J] 

[Okay, but we’ll take it easy. I gotta go, my mom’s getting impatient about the movie. ttyl? -R]

[Of course. I’m gonna enjoy my high for now. Bye Booktease. -J]

[Bye Dodger. -R] Rory put her phone down with a grin.

“Finished?” Lorelai asked. “Because the movie cannot wait forever.”

“Yes, sorry, Paris was being...well, Paris.” Rory made a face. 

“Well that grin was definitely not something I associate with your dealings with Paris, unless you finally managed to one-up the little…”

“I did, in fact.” Rory beamed. 

“Well then we celebrate! Pizza for all!” Grabbing the phone, Lorelai dialed the pizza place. “Hey it’s Lorelai. Yep the usual. See ya in a few.”

Rory pressed play on the movie. About 10 minutes later, their pizzas arrived.

Lorelai answered the door and grinned. “Ohh just in time. We thought we might have to break down and actually eat the salad Sookie stuck in the fridge. Thanks!”

The delivery smiled and headed out. Rory grabbed a plate and got two big slices.  
“Happy?” 

“Very.” The rest of the night went amazingly. Snacks and movies galore. The Girls ended up falling asleep in the living room.

**Notes for the Chapter:**

> More updates tomorrow!


	5. The Point Of No Return

The rest of the week had flown by and suddenly, it was Saturday morning. “Rory, calm down,” Lane said. “I’m sure it’ll be fine.”

Rory took a deep breath. “You’re right.” She smiled and hooked arms with Lane. “Lets go!” 

With a grin, Lane accompanied Rory downstairs. “Are you driving or is your mom taking us?”

“I’m driving.” Rory dangled the keys to the jeep and got in the drivers seat. 

“Sweet!” Lane hopped into the passenger seat and grinned. “To Hartford and your new man we go!”

Rory blushed and pulled out of the driveway. It took about 20 minutes to get into Hartford. Jess’s bus had pulled up and docked at the station just as they got into the city. 

Rory, seeing the bus at the station, excitedly pulled into the parking lot and hopped out, scanning the crowd for Jess. Upon spotting him in his leather jacket clad glory, she called out, “Jess!!”

Jess turned at the sound of his name, he spotted Rory and grinned as he made his way over to her. His black eye was gone but he still had his ribs taped up beneath his shirt and the bruising hadn’t really gone down at all. 

Rory tried to surreptitiously look him over to make sure he was okay as he drew nearer but by the obvious eye roll, knew she had failed to be sneaky.

Jess pulled her into his arms when he was close enough. “I’m fine, stop worrying.” 

“Considering I can feel the tape on your ribs,” Rory said into his chest, “I’m slightly worried, but I’ll try to stop.”

Jess sighed. “I brought the pain killers if that helps? Plus, you owe me a kiss.” He grinned. “It’ll make me feel even better.” 

Rory rolled her eyes and grinned. “That’s good to know. And I do? I don’t remember that at all,” Rory teased.

“I can show you the text.” Jess teased back.

Rory considered for a second. “Alright. I believe you.” Quickly she rose on tiptoe and dropped a quick kiss on his cheek. “There.”

“Allow me?” Jess asked, his eyes locked with hers. 

“Allow you what?” Rory felt somewhat dazed just from kissing his check. His aftershave or cologne smelled wonderful, indescribably alluring.

“This.” Jess replied softly before he leaned down and kissed her rather gently on the lips. A few feet away Lane quietly flailed a bit. 

For a few seconds, the rest of the world seemed to be at a standstill. As Rory and Jess pulled away from each other, it sped up to catch up to where it was supposed to be.

Jess was smiling and took her hand in his. “Come on.” 

Rory nodded, slightly giddy, and led him over to the car. Lane had moved into the back so that Jess could sit in the passenger seat, and Rory helped him climb in so as not to jostle his ribs too much. After getting him settled and running around the front of the jeep, she swung herself up into the driver’s seat and started the car. “And off we go!”

Jess laughed a bit and settled in. “Where to first?”

Lane chose that moment to speak up. “I was thinking lunch?”

“Jess?” Rory asked.

“Lunch sounds good,” he replied. 

“Lunch it is!” Rory announced, heading towards downtown. “What’re we in the mood for?”

“Whatever you want.” Jess said. 

“Lane?”

“Somewhere I can get a sandwich. What’s that one place we went to last time we came shopping?”

“Vivian’s?” Rory suggested. “That place with the awesome croissant sandwiches right?”

“Yes!” Lane exclaimed.

Rory had them parked out front in less than 5 minutes, Jess had his arm around Rory as they walked in. 

Inside, they quickly found a free table that would fit all three of them and Jess pulled Rory into his side as they sat. Rory’s grin appeased any objection Lane might have voiced. Jess pressed a kiss to Rory’s lips just before he picked up the menu.

Tristan, Paris & co, and a few other Chilton students just so happened to be walking by at that particular moment. “It appears Mary, really is more of a Maggy..” Tristan pointed out. 

“Oh my God,” Paris muttered. 

“Who’s the hottie?” asked Louise, her smile coy.

“Wait, that’s not her boyfriend,” Madeline said, confused. “What even?”

The waiter stopped at their table and Jess, Rory and Lane ordered. Jess then moved to put his arm around her.   
Louise grinned. “Well either they broke up or she’s cheating on him.” 

Tristan remembered the number and name he’d seen on Rory’s hand in New York. “Wait, I think I know who that is.”

“Who?!” Louise asked eagerly.

Paris rolled her eyes and pushed past the others to continue on her way. “I don’t know why you’re so fascinated with her life.”

“When we were in New York I noticed a name and number on her hand. Jess something. I bet that’s who’s with her.” 

“Makes sense,” Louise said.

Madeline was still confused. “But...why would she break up with or cheat on her boyfriend? He’s perfect.”

“Maybe because she’s a manipulative little gold-digger like her mother,” Paris said haughtily.

Louise frowned a bit. “Jess or whatever his name is doesn’t look any richer than her last boyfriend.” 

“Looks can be deceiving,” Paris responded sharply. “For all we know, his dad’s a super rich mob boss.”

Amidst their bickering the trio inside had finished eating and were now heading for the door. “Guys, we need to hide!” Madeline all but shouted. 

Tristan jumped a bit and grabbed Paris, pulling her with him over to the brick wall next to the door and pressing her up against it so that their faces were hidden behind hair and a turned head. “Shit,” he whispered.

“Tristan!” Paris hissed. “You’re on my toe!”

Tristan shushed her as the trio exited the cafe. 

“Honestly, Rory, I’m glad you and Dean broke up, I like Jess a lot better.” Lane said to the pair. 

Jess grinned. “Yea, Rory.” 

Rory laughed and Tristan felt his heart skip a beat. “Well I’m glad you approve Lane. Because otherwise this would be a very awkward day!”

Lane simply laughed and shook her head.

“Bookstore? You promised me books.” Jess asked as the trio continued down the sidewalk.

“Let’s follow them!” Louise whispered. 

Paris shook her head fervently. “No! We have better things to do than --”

“Yes!” Madeline and Tristan said eagerly. 

“Good,” Louise said. “Let’s go.”

The bookstore Rory led them to was a rather massive place, 2 floors and everything. “Wow, you outdid yourself, Gilmore.” Jess said fondly. 

Rory smiled proudly. “I try Mariano.”

Paris, who had overheard the conversation, stopped, forcing the rest of her small posse to stop as well. “Did you hear that? Mariano. You guys know who the Mariano’s are right?”

Louise, Madeline and Tristan shook their heads. 

“They’re the biggest mob family on the East Coast. Italian, Irish, any of them. The Mariano’s are the biggest. And I’d be willing to bet that Gilmore doesn’t even know.”

Louise and Madeline went wide eyed. “Oh my god… but...maybe he isn’t related?” 

“The chances of that? Slim to none. Mariano isn’t exactly a popular name.”

“Damn.” Tristan muttered. 

Paris nodded. “It’s a wonder she hasn’t found a gun on him already.”

“I’ll give you two lovebirds some time. Meet ya back at storefront in an hour?” Lane smiled. 

“Okay,” Rory responded softly. With a grin, she grabbed Jess’ hand and led him off towards the older books.  
Jess quite happily followed her, this part of the bookstore was rather secluded and didn’t get much traffic. 

Tristan, Louise, Madeline and Paris followed the pair.

“So, anything in particular you’re looking for today?” Rory asked politely.

“Surprise me, Booktease.” Jess said fondly. 

“Careful, Dodger. What if I pull some Rand for you?”

“Then you’re getting Hemingway.” Jess teased. 

Rory made a face and began walking along the nearest shelf, trailing a hand loosely against a row of books.   
“Point made, Jess. Hmmm….” She thought for a moment and then stopped, tapping a book’s spine thoughtfully before pulling it and handing it to him. “Jane Austen’s Emma.”

“Good choice. Been awhile since I read any Austen.” 

“Oh God, are they flirting over books?” Louise muttered.

Tristan grimaced. No wonder he could never convince Rory to go out with him.

Rory grinned. “Alright your turn. Pick something for me?”

Jess led her a ways down and selected Franny & Zooey by J.D Salinger. 

“I haven’t read this in ages. Wow.”

Jess grinned and slid his arms around her again. 

Rory nuzzled her head into his chest and smiled. “I missed you,” she admitted quietly.

Jess kissed the top of her head. “Missed you too…” he took a deep breath. “And sorry for the worry I caused...” 

Rory shook her head, face still buried in his chest. “It’s okay. I just...It sounded really bad, and when you said that leaving wasn’t an option because someone always drags you back and I said it sounded like the mob, you seemed to get sort of panicky. That was what made me worry the most.”

Jess tensed up considerably. “Rory…”

“What?” she asked, looking up at him finally. “I wasn’t being serious but if you really were part of the mob you’d tell me right?”

Paris had to forcibly hush her gasp. “I knew it!” she hissed. “She doesn’t know.”

Jess pulled back a bit and ran a hand through his hair. “Shit, Rory, and what would that do exactly? Give you more to worry about?” He looked up at her, his expression confirmed what he didn’t dare say out loud. 

Rory shrugged. “I’d rather know and have specifics to worry about than just a sort of general worry. General worry is a lot harder to-”

Jess moved close to her again and whispered in her ear, so that only she’d hear. “Rory, for now, leave it? This isn’t the time or the place for this kind of conversation.”

Rory nodded and turned her head slightly to look at him. She had the sneaking suspicion that he really was part of the mob -- he’d all but confirmed it -- but she would respect his request to drop it for now. “Okay. But, you will, eventually…?” She tried her hardest to communicate her desperate desire to be fully included in his world through her eyes and expression.

Jess nodded, coffee colored eyes locking with hers. “Promise.” 

Rory smiled somewhat bashfully and ducked her head.

“God she’s such a dweeb,” Paris muttered.

“That’s so sweet,” Madeline murmured.

Jess tilted her chin up so she had to look at him before he leaned in and kissed her, gently at first.  
Tristan made a face. 

Rory grinned and as they pulled away, she said, very quietly, “I really like you.”

Tristan huffed indignantly, Paris rolled her eyes and Louise and Madeline fought to restrain giddy giggles of joy.

Jess’ heart felt that little tug of affection again. “I really like you too Rory.” Jess smiled playfully. 

“Good. Because I don’t intend to be letting you go any time soon.”

“Good, I don’t want you to.” Jess slid one hand to her hips and the other bracketed them against the bookcase.   
“Okay she is officially the luckiest girl alive,” Louise said, slightly jealous.

Madeline nodded. “I bet he’s super toned…”

Tristan shook his head and walked off, he’d had enough.

Paris, finally completely fed up, snapped, “Well I hope she’s happy with her mob boss boyfriend. Now I’m leaving.” Angrily, she stomped off after Tristan.

Louise and Madeline shared a look. 

“Looks like people are jealous,” Louise said craftily. Madeline giggled and nodded.  
Jess really wanted to kiss her again. 

Before he could do anything, however, Rory grinned and said, slightly louder than a normal speaking voice, “I sure hope you all enjoyed the show, but if you don’t mind, Louise, Madeline, we’d like to be left alone now?”

The girls tripped over themselves as they stood up. “Uh..Bye Rory! Er...Rory’s boyfriend!” They quickly ran off.

Rory giggled. “Sorry. Classmates. Spying. Don’t know why.”

“Huh. Maybe they’re jealous.” 

Rory shrugged. “More likely they want juicy gossip.”

Jess didn’t care all that much, he had far more interesting things on his mind.

The moment of silence stretched on until, finally, Rory asked, “So are you gonna kiss me or…?”

Jess responded by kissing her once more, pressing her up against the bookcase as he did so. 

Rory responded enthusiastically, her back pressing against the shelves as if it was the only thing keeping her standing.

Jess wasted no time in deepening the kiss; they were pressed all the way up against each other by now.

It was like nothing else mattered except the feel of his lips, his body pressed against hers, and it didn’t even matter that she could feel the rib tape through his ungodly thin tshirt or that her back hurt, because all of a sudden she could really truly feel something. Everything was vivid, like someone was searing the experience into her brain. And she relished that.

Jess moved the hand that had been bracketing them against the bookcase into her hair, and decided to trail kisses down to her neck as well. He was utterly and completely gone on her; brain nearing sensory overload. 

Rory’s breathing was slightly faster than normal, but her heart rate...it felt like it was through the roof, she was so happy. “I feel alive,” she murmured.

“M’ glad.” Jess murmured. He was tempted to leave a mark, but he wasn’t sure how she’d react to that. 

“Just don’t…” Rory swallowed, trying to calm her racing heart. “Don’t leave a mark where my mom could see it, okay? She doesn’t know about you yet.”

“Noted.” Jess tugged her collar down a bit further and pressed a kiss to the spot he wished to make the mark. 

Rory groaned a little and muttered, “Tease.”

Jess took that as initiative and bit down, just enough to make a point, but not enough to leave any real mark. 

She whimpered a little, and one hand crept into his hair to rake patterns on his scalp with her finger nails.

Jess made a pleased sound and bit just a little bit harder. Her hands in his hair made his thoughts cloudy and he really had to work to focus on the task at hand. 

“Jess,” Rory whispered, her voice breathy.

Jess continued for a few moments and only pulled away when he was satisfied with the mark. When he looked at her, his pupils were blown wide. 

Her eyes were heavy looking, almost like she was tired but not quite.

Jess kissed her again, this time it was slow, and sweet, and almost maddening. 

“Next time,” Rory said breathlessly, “I’m marking you so all those New York girls know to back off.”

Anything further was cut off by Lane’s voice drifting towards them across the stacks. “Rory? Jess? Are you guys up here? We were supposed to meet downstairs fifteen minutes ago!”

“I’m holding you to that.” Jess reluctantly pulled away. 

“Sorry! We...uh... got distracted.” Rory blushed.

Lane took in their appearances and grinned. “I see that.” 

Jess helped Rory smooth out her hair and she gave his a playful tussle. They grabbed their books and went to checkout. Lane sent Rory a look that meant ‘I better get details later.’ 

A few moments later they exited the bookstore. 

The afternoon seemed to absolutely fly, leaving Rory’s head spinning. As they walked towards the theater that evening, bags of books in hands still slightly sticky from melty ice cream earlier. Their tickets, waiting for them at will call, were some of the best seats available, courtesy of Rory’s grandmother who thought it was an “excellent idea” that Rory take in a show with some friends.

Jess held the door open for both Rory and Lane. They had about 10 minutes until show time. They were handed their programs and showed to their seats in a matter of moments. 

 

As they settled into their seats, Rory happened to look up. “We are directly under the chandelier,” she said interestedly.

Lane followed her gaze. “Yes we are. Guess it’s a good thing we have a big strong guy with us to save us as it falls.”

“Lane.” Rory’s tone was lovingly exasperated. “Jess is injured. We’re more likely to be saving him.”

Jess made a face. “I’m perfectly fine, a few broken ribs are nothing.” he muttered. 

“I wouldn’t call them nothing since you couldn’t breathe,” Rory chided. “I swear. Men.”

Lane just looked at them. “What even…?”

Rory shrugged. “We just get each other.” Before another word could be said, the orchestra began tuning and the lights began to dim. Showtime.

Jess grinned at Rory before focusing on the stage.

Jess took Rory’s hand each time just before the chandelier fell, having had the show memorized from the many times he’d seen it. 

Her gasps of delight and slight fear as she squeezed his hand went unnoticed by Rory as she lost herself in the show.

Jess, of course, noticed. He was happy she was enjoying herself. He himself perked up at The Point of No Return. It was one of his favorite numbers. He silently mouthed the words along with the Phantom. 

Rory caught sight of him mouthing along out of the corner of her eye and grinned before snuggling into him. He was a goofball, but she was pretty confident he was her goofball.

Jess blushed a bit but didn’t stop. 

The rest of the show went by all too quickly for both Rory, Jess and even Lane’s tastes. 

As they clapped and cheered for the curtain call, Rory fought to keep a smile on her face. The end of the show meant the end of her night with Jess. Right then and there, Rory made a decision. She would surprise him Tuesday night.

Jess walked Lane and Rory to the car; he wasn’t looking forward to saying goodbye. He’d miss her terribly. Fighting back a sigh he forced a smile and pulled her into his arms. 

“Jess,” Rory said quietly. He shushed her a bit but she continued. “Jess I had a really great time and I don’t want you to go.”

Jess pressed a kiss to the top of her head. “I don’t want to go either, but we both know I have to.” His voice was soft as he spoke. “I’ll miss you...”

“I’ll miss you more,” Rory said softly. Looking up at him, she said, “Call or text when you get home?”

“Of course, and before I forget...” He placed her now annotated copy of Howl into her bag. Jess then kissed her in a way that hurt his chest and took his own breath away. God, would he miss her.

As she pulled away from a kiss that could only be described as heartbreaking, she felt her heart seemingly reach for him as he backed away towards the waiting bus.

Jess boarded his bus and met her eyes through the window. 

She sniffled and waved. He’d been the last to get on and now the bus was starting up, spitting puffs of exhaust into the night.

He waved to her and watched her till the bus drove out of sight and he could no longer see her.

Holding back tears, Rory unlocked the car and climbed in, trying her hardest to put on a neutral expression.

“You’ll see him soon,” Lane said knowingly. Rory nodded, started the car, and pulled out of the parking lot. Tuesday could not come soon enough.


	6. Junk of the Heart

**Notes for the Chapter:**

> This chapter is quite a bit longer than the others, you'll see why.

Jess Mariano walked down the seedy back alley between The All Saints Tavern and a Mariano family owned apartment building. Mostly dealers and basement level ‘employees’ lived there. It was one of his main rendezvous points, but frankly Jess hated it. Everyone constantly underestimated him, especially the men he met with here. He was Jimmy Mariano’s heir for fucks sake and underestimating him would mean the worst for them in the long run. Jess continued on till he was directly behind the tavern in a sectioned off courtyard.

Adjusting his collar and suit coat, he went over his instructions and took in his surroundings. Jess was in a gorgeous black suit, no tie and the first button of his crisp white dress shirt was undone. He had on black oxfords and his leather dual gun holsters were hidden beneath his suit coat. 

His contact entered the courtyard a few minutes later; however he entered with two clearly armed guards.  
“What the fuck is this?” Jess gestured to the armed men behind Armand. 

Armand didn’t take to kindly to Jess’ attitude. “Show some respect boy.” Armand sneered. 

Before any of the three could blink Jess had drew his gun and fired a round each into the guards’ heads. “I think you are the one who needs to show some respect.” Jess tucked his gun back into the holster. “My father may be in The Seat, but who do you think handles everything else? I do. I. Run. This. City. I am your boss and you will show some fucking respect!” Jess was shouting by this point. Armand was scared silent; clearly he’d made a mistake underestimating the Mariano heir. “M-My apologies sir! It won’t happen again.” 

“Damn right it won’t. Now, hand over what you came here for.” Jess was the peak of composure by this point.  
Armand opened the briefcase and displayed the contents before handing it over to Jess.

“Now get out of here. And it’d be in your interest to spread around the level of respect that best be shown to me.” Jess spoke in a cold and deadly tone.

“Yes sir.” Armand quickly hurried away. 

Jess entered The All Saints Tavern from the back entrance and sat down at the bar. “I’d suggest you clean up the court yard.” Jess said pointedly. 

The barkeep’s eyes widened -- he hadn’t expected that from the Mariano heir. “Right away...in the meantime may I get you a drink?” 

“Martini, Gin not Vodka.” 

“Right away sir.”  
\----  
Jess headed home afterwards to his new residence, his father had gotten him a new flat in the Hell’s Kitchen/Midtown are. It was a….classy place to say the least; tailored especially to a bespoke lifestyle. Jimmy had made it clear that Jess was ‘free’ to do as he pleased and live on his own as long as he stepped up and took charge of what was expected of him. Jess agreed, of course. He pressed the penthouse level the moment he stepped into the elevator and sighed. Breaking the news of his new residence had been interesting to say the least. He was used to living in seedy flats and rough neighborhoods while his dad did god knows what and lived in some ritzy joint. It was still taking some getting used to, to be honest. The elevator dinged and he stepped out onto the penthouse floor. He grabbed his key and let himself in.  
\----  
Rory’s cab stopped just outside of his building. “Woah,” she said under her breath. Quickly, she paid the cabbie, and made her way to the door. “Hi,” she said hesitantly to the doorman.

“Good evening miss. Anything I can do for you?”

“I’m looking for Jess Mariano? Would you happen to know..?”

“Where to find him?” the man chuckled. He had a nice smile. “I do believe Mr. Mariano has penthouse a. If you head straight through these doors and turn left just past the desk, you’ll find the elevator that can get you there. Should I let him know you’re coming up?”

Rory shook her head. “I’m here to surprise him. Thank you so much.”

“You’re very welcome. If you need anything else, Sarah’s working the desk tonight and she’s the sweetest thing this side of the river.” He tipped his hat as he pulled open the door. “Have a nice evening Miss…?”

“Gilmore. Rory Gilmore.”

“Have a nice evening Miss Gilmore.”

Grinning, Rory stepped through the door and followed the directions she’d been given for the elevator. Nervously, she pressed the button to call it and waited.

The elevator dinged almost immediately and quickly took her up to the top floor. It let her out in Jess’ hall right by his door. 

Before she could wimp out, Rory walked to his front door and rang the buzzer. Immediately, she was fighting not to panic. What if he wasn’t in? What if he had another girl with him? What if his dad was here too?

Inside the penthouse Jess’ moved to the bar, his oxfords loud against the hardwood floors. He needed a drink before anything else. 

Before he could reach the bar and the heaven that would be alcohol, the buzzer sounded. He debated whether or not to answer until a timid knock sounded on the door.

Jess kept his hand on one of the guns in his holster as he went to answer the door, but when he swung it open his eyes widened in shock. “Rory? What..?” He couldn’t even string together a proper sentence but very quickly took his hand off the gun. 

“Surprise!” Rory said faintly. Her face was pinched, and she looked towards his hand as he pulled it away from the gun. 

Jess motioned her inside, and shut and locked the door behind them. “I...wasn’t expecting anyone. Uh...let me…” He shrugged off his suit coat and quickly undid the holsters and laid them on the table.

Rory was surprisingly quiet, watching him do these things almost as if nothing was wrong. Shock, probably. Finding your boyfriend packing as heavily as he had been tended to do that to a girl. As he turned around, Rory gasped. “Jess, please tell me that is not your blood on your shirt and the toe of your shoes,” she said quietly, her voice slightly menacing.

Jess looked down and quietly swore. “Jesus fucking...No, no it’s not my blood. Rory I am so sorry.” He ran a nervous hand through his hair. 

“Why are you apologizing?” she asked, her voice still quiet. Eerily so, like the calm before a huge storm.

“I didn’t, don’t want you seeing me like this.” He bit his lip. 

Rory squinched her eyes shut and moved over to the couch. “I think I need to sit down,” she murmured.

Jess nodded. “I’m...I’m going to go change and uh, put them away. Then we can talk..Water is in the fridge.” He gave her one last look before he left the room with his guns and holsters. It took him maybe 5 minutes at most to get changed into jeans and a tshirt. 

While she waited, Rory drifted to the kitchen and got some water before drifting back to the couch, setting her glass on the glass and chrome coffee table. Even in her somewhat dazed state, she noted that Jess had a very nice place.

Jess walked back into the room and took a seat next to her with an expression of worry on his face.  
Aimlessly, Rory looked out the window and picked up her glass to fidget with it.

“Rory?” he asked softly. “Please look at me.” 

Almost blankly, Rory did as he asked. Her eyes were a funny sort of blank that gave Jess the feeling that she was making them that way on purpose.

Jess took a shaky breath. “I think we should have that conversation now…”

With that, Rory snapped back to herself, her eyes sparking hotly. She sat her glass back on the table with a definitive clink of glass on glass and turned to look at him, crossing her arms over her chest. “I agree. Talk.”

Jess quickly downed his now warm drink before he started. “I think based on what you saw...that…that I am in fact part of the mob.” Jess took a painful deep breath before he continued. “I didn’t choose this life, I was born into it. My father is Jimmy Mariano…” 

Rory shook her head. “Should the name mean something to me?”

Jess blinked a bit out of surprise. “Probably better that you haven’t heard anything… Uh, we, the Mariano Family run New York. Actually to be honest we control the majority of the East and Midwest. We have a few places out west like parts of Los Angeles, San Francisco and Las Vegas. But our main powerhouses are New York and Chicago. My father is the head of the family, I’m his only heir.”

It was Rory’s turn to blink. “So when I mentioned the mob and you got all panicky, and then at the bookstore...And you wouldn’t just tell me because?!” She was mad.

“I’ve been worried out of my mind, thinking I must be crazy because really what are the chances of meeting a teenager who’s part of the mob? And despite having some decent evidence, I decided to ignore it and trust that since you hadn’t said anything, then it was probably something else entirely. Seriously Jess. This is kind of something you tell a girl before she likes you enough to surprise you at your apartment!”

Jess had his head in his hands, but lifted them once she quieted. “Rory I’m sorry! This isn’t exactly the kind of conversation you have in public! Especially with people eavesdropping on us! Furthermore, you heard me promise you that we’d talk. Hell, I was planning on calling you after I’d had a drink and cleaned up! I care about you, so much. It physically hurts to not be around you. I don’t like keeping things from you, but I’m not going to have important, slightly dangerous conversations with you in public!” 

“How many times have we talked since then, hm?” Rory asked. She seemed calmer. “I understand not talking about in in public. Hell, that makes sense. But before that? And after? In all the phone calls and text messages, not once did you think to say, ‘By the way, Rory. You were right. I’m part of the mob!’ or ‘My dad runs the Eastern seaboard and the Midwest.’ Honestly! Did you not trust me or something?”

“No! That is definitely not the reason! I wasn’t about to just drop a bomb like that over the phone. Do you or do you not agree that this is a conversation best had in person? Not to mention I’m constantly worried he’s bugged my phone.” Jess got up and got himself a refill. 

Rory pulled herself to her feet and crossed the few feet to the wall of windows. Her reflection stared back at her, eyes wide and full of emotions too complicated to describe. All at once she was relieved that she had been right, that Jess really was in the mob, but she was hurt he hadn’t told her. She understood his reasons, but it still hurt. And somewhere, jumbled up amidst the raging little inferno of hurt anger, was how she felt about him. She was pretty sure she loved him, and she definitely cared about him more than anyone else. When he’d said that it physically hurt to be away from her, she’d fought the urge to throw herself into his arms and cry hysterically.

Behind her the sound of glass shattering echoed throughout the room. “F-Fuck...” Jess was shaking so much he’d dropped the glass; he braced himself against the bar, head bowed, breaths becoming shallower and shorter as his heart pounded away. He squeezed his eyes shut. 

Having turned at the shattering sound, Rory crossed the room and tugged him gently away from the bar, pulling him towards the couch so she could pull his head into her lap to run her fingers through his hair. “Ssshhhh,” she whispered gently. “Ssshhhh.”

Jess trembled and couldn’t stop the tears that ran down his cheeks. This wasn’t supposed to happen. He never let anyone see him like this. But everything had just gotten to be too much, he had already been stressed from the events of the day then this conversation had just pushed him over. Jess was worried, scared; he couldn’t bear to lose her, but he also knew she may not be safe with him. He’d do whatever it took to ensure her safety though. It was pretty evident at this point that he’d fallen in love with her, and fallen hard. 

Rory kept running her fingers through his hair, gently hushing him and eventually humming something gentle, although for the life of her she couldn’t remember the name. As he started to calm down, his breathing becoming less gasping, his tears less frequent, she pulled him up so his head rested on her shoulder and pulled him close, rocking gently.

Jess slowly allowed himself to relax and let his breathing even out. “Sorry…” he mumbled.

Rory shook her head and pressed a kiss to the crown of his head. “No, I’m sorry. I shouldn’t have yelled at you. Are you okay?” she asked gently.

“M’fine now.” He turned to nuzzle against her neck. 

Rory shivered slightly. “G-good.”

Jess lifted his head and turned to face her, meeting her eyes. 

“Jess,” she said quietly.

Jess responded by kissing her. 

For a few moments, Rory was pretty happy to stay right where she was. But before long, the need to speak her mind won out. Pulling away, she looked him dead in the eye and said, “You know I’m not going anywhere right?”

Jess’ heart sped up a bit at that. Relief washed over him. “I’m glad.” he nearly cringed at how his voice wavered. 

She dropped a quick kiss on his nose. “Good. Because we’d have an issue if you weren’t.”

That got a smile out of him. “Can you stay the night?” 

Rory nodded slowly. 

Jess broke out in a grin. 

“Don’t get ahead of yourself, Mariano,” Rory warned playfully.

“Mhm. Whatever you say Gilmore.” He stood up and stretched, his tshirt riding up a bit. “You hungry?”

For a hot second, it was all Rory could do to even maybe process that he was speaking as she caught sight of skin at the edge of his tshirt. “I’m sorry?” she asked, with a noticeable shake of her head.

Jess smirked, noticing of course. “Food? Yes or no?”

She shook her head slightly again. “Uh...yes. Please.”

“What are you in the mood for? I could make pizza, pasta, anything really.” 

“Oh just a sandwich is fine. It’s late and you seem like you’ve had a really long day, babe.”

“Compromise, I’ll make burgers. That good?” Jess forced to keep himself from grinning at her use of ‘babe.’

Rory grinned and rolled her eyes. “Fine. While you do that then, mind if I take a shower? The bus ride was kind of gritty.” 

“My bedroom is the last door at the end of the wall, and has the best shower, so feel free. My tshirts and sweatpants are in the first two dresser drawers.” 

Rory scrunched up her face. “Is that your way of saying don’t go rifling through your drawers? Because let me tell you, that ruins all of my plans.”

“Rory, go crazy, I honestly don’t care just….don’t touch the safe. I didn’t lock it when I uh… put the...” Jess trailed off. 

“When you put the guns away. Okay,” Rory shrugged. “Noted. I’ll be back, sir.”

Jess kissed her cheek before she walked away; he shamelessly watched as she went. 

As she made her way towards Jess’ bedroom, Rory took note of the very chic decor. The off-white walls managed to be open and cool yet inviting, and the art was just bright enough to draw your eye but not overwhelm. She stopped just in front of the door. It was cracked, and she felt almost like someone had punched her gut. She’d never been into a guy’s bedroom before, let alone a boyfriend’s, and she was sure Lorelai would kill her if she found out. But she needed a shower and clean clothes because, really, she hadn’t planned ahead very well and had managed to get to New York without pyjamas. Taking a breath, she gently pushed the door open and felt her eyebrows raise. The room was a decent size, and very neat. Not at all what she had expected. There were posters framed on the walls and blackout curtains covering the large window on the wall. His bed was a massive California King with black bedding. There were tasteful white accents among the black. On one wall was the door to a walk in closet and next to that was the bathroom door. On the wall with the entrance to his bedroom was a massive floor to ceiling bookcase that stretched the expanse of that wall. Tucked into the corner was the safe --the size of a small night table -- not locked but closed. Rory gave it a wide berth as she made her way into the bathroom. The lights glinted softly on the chrome fixtures and beige mosaic tiles lined up in a stripe on the wall like a chair rail. The marble floors and counter lent themselves to a dull echo as she walked across them, her shoes tapping with every step. Quietly, as if she would wake the dead otherwise, Rory found the shower’s controls and made sure she knew how to work them and adjust the water before stripping down. Knotting her hair on top of her head, she stepped into the absolutely huge shower stall with rain heads and turned on the water, relaxing into the warm spray almost immediately.

Jess had dinner well underway in the mean time, but couldn’t stop his thoughts from wandering back to Rory. All he could think about is how she was currently dripping wet and naked in his shower. He shook his head and bit down on his lip. He really did not need a hard-on right now. 

Rory was somewhat lost in a dream as she rinsed away the soap suds. It was true, generally, that Rory was in and out of showers very quickly. But this one...Jess had not been lying when he said it was the best. As her mind drifted, images of Jess coming looking for her, finding her still in the shower, joining her crossed her mind before she mentally shook herself. The water started to run a little cooler, and Rory took that as her sign to finish up. Turning off the water and hopping out, she grabbed an incredibly fluffy towel and wrapped it around herself to go look for clothes. The bathroom, luckily, had its own entrance to the closet, shortening the distance Rory had to travel for clothing. Remembering that Jess had told her his tshirts were in the first two drawers, she pulled open a drawer and went to grab one, not really caring which one, and then went on the hunt for pants. He’s mentioned sweats but honestly, Rory thought it was kind of warm in the apartment for those and instead opened and closed drawers until she found his boxers. Grabbing a pair, she ducked back into the bathroom to make sure she was dry and hop into the borrowed clothes. Deciding to leave her hair up and out of the way, she hung the towel back on the rack and flipped off the lights, before heading back towards the kitchen.

Jess had the table set and food plated, he was bringing their drinks in just as Rory walked into the kitchen. He looked up and nearly whined. She was in his clothes, even better, she wasn’t wearing pants… Jess let his eyes roam over her before meeting her eyes. His eyes were akin to black coffee by this point. 

Rory felt herself blush, just a little, as she scootched past him to sit down at the table. Tucking a leg beneath her, she gracefully dropped into a seat and turned her head to look at him. “The burgers smell wonderful, Jess.”

Jess finally snapped out of it and took a seat as well. “Thanks,” he replied with a smile.

Rory, quickly, took a sip of her drink and made a funny face when she noticed what it was. “Red wine?”

Jess’ cheeks flushed a rosy color. “Do you not like it? I can get you something else…”

“Oh no, no!” Rory responded quickly. “I just wasn’t expecting it! My mom doesn’t really let me have any alcohol except at Christmas, so normally when there’s a liquid that color in a wine glass for me it’s grape juice.”

Jess smiled a bit at that. “I pretty much always have wine with dinner. It’s an Italian thing I guess.” 

Rory smiled and looked down for a second before looking back at him. “Well, I look forward to sharing more wine with you then.”

Jess flashed a smile her way before taking a sip of his own wine.

Looking for any way to distract herself from staring at him longingly -- God she wanted him to kiss her -- Rory set her glass back down and picked up her burger. Taking a bite, she couldn’t help but moan as she savored the absolutely amazing burger Jess had made her.

Jess ate via autopilot, his thoughts were too occupied with Rory. 

Rory continued to enjoy her burger, somewhat oblivious to the obvious preoccupation Jess had with her. Between the wine and the burger, Rory was pretty sure she never wanted to leave.

Jess finished up his burger a few minutes later and leaned back to watch Rory as he drank the rest of his wine.  
She sipped at her wine, barely making a dent in it, her head feeling a little lighter but not gone. As she munched away at the last bits of her burger she did her best to shove her thoughts about Jess into a tiny little box in the corner of her mind.

Jess stood up and took their plates to the sink. 

Rory stayed seated, hoping that if she just stayed there, Jess wouldn’t notice the way his smile made her knees go all wobbly.

When Jess came back he downed the rest of his wine. “Sofa?”

“Su-sure,” Rory said, barely controlling the stutter in her voice under the intensity of his gaze.  
Jess held out his hand to her. 

Doing her best to control her shaking, Rory accepted his hand and stood up, taking her wine glass with her. She really didn’t need the alcohol but it gave her something to do with her hands besides throw herself at Jess.  
Jess led her to the sofa, gently taking the glass from her and set it on the table before pulling her onto his lap.  
Without thinking, she curled into him, her head on his shoulder and her legs drawn up fully into his lap, one forearm resting against his chest. She sighed in relief as a feeling like elastic stretched too tight eased somewhere deep in her soul.

Jess pulled at the elastic around her bun and ran his fingers through her hair, content and absolutely loving having her so close. 

She moaned quietly and her head tilted towards his hand, searching for more pressure against her scalp than he was offering.

Jess bit his lip and his eyes closed for a moment, but didn’t stop running his fingers through her hair. She moaned, he hadn’t been expecting that. It certainly sent a rush of blood south. 

It was a magical feeling, Rory thought, having someone you love run their fingers through your hair. And when Jess did it...well her mind wasn’t exactly worthy of the “Mary” Tristan often threw her way at school.  
Jess couldn’t help but press a gentle kiss to her neck, just above where he’d previously marked her. 

She let out a little high-pitched whine and her hips wriggled a bit in his lap as she tried to get comfortable again.

Jess let out a soft moan and slid an arm around her waist. He was more than half hard by that point and her wriggling about only furthered that. 

Rory sighed somewhat breathlessly and turned so that she was facing Jess.

Jess’ pupils were blown wide and the way he looked at her could only be categorized as blatant eyefucking.

Rory could feel her face heating up with a blush but she couldn’t look away. Something about Jess’ stare was nailing her in place, and, strangely enough, she didn’t want to look away. She bit her lip.

“Rory…” Jess’ voice came out rougher and just a bit deeper than usual, his accent was thicker too. 

Rory tried to respond but all she could manage was a “mm?”

Jess answered by kissing her, but unlike the other times this was a bit rougher, more desperate. One hand tangled in her hair as the other slid to her hip. 

For a second, Rory was shocked, unable to respond. But then her body unlocked and she responded with just as much desperation, a need to get as close as physically possible. She moved to straddle Jess’ lap, one leg dragging across his lap as she rearranged herself while her hands plunged into his hair, nails raking gently against his scalp.

Jess couldn’t help but moan and roll his hips upward to try and get better friction. He deepened the kiss further, out of pure need. 

Rory moaned and pressed closer. And still closer. Nerve endings sparked and she was fairly certain she couldn’t press any closer.

Jess broke the kiss for a fraction of a second. “Bedroom.” He then resumed kissing her breathless as her picked her up and carried her down the hall and into his room. 

Without thinking, Rory dug her heels into the top of his ass, loving that it pulled her even closer, loving the feel of his toned stomach through his thin tshirt.

Jess broke the kiss and let out a rather filthy moan. He kicked his bedroom door shut and wasted no time laying her down on the bed. 

Greedily, Rory pulled his face back to hers, kissing like a woman who knew she was going to die tomorrow.  
Jess matched her exactly in that department; he couldn’t help but to grind down on her a bit either as he ran his fingertips just above the hem of the tshirt she was wearing. 

She whimpered pitifully and squirmed away from his fingers, because it honestly tickled, just a little. Her hands in his hair tugged gently, enjoying the feel of the strands between her fingers. 

“Rory…” Jess all but whined against her shoulder, as he retaliated by nipping her. 

Her heels sank lower on his ass and pulled his hips closer, her lips brushing the underside of his jaw teasingly. 

Jess took that as initiative to properly bite and mark there. 

Rory’s lips continued to brush against his jaw, his neck, that spot just behind his ear. Interspersed with those brushes of lips were tiny nips, just enough let him know she meant business.

“Such a tease,” he murmured, hand sliding up the back of her tshirt to the small of her back. 

She gasped and nipped at his neck a little harder. “Speak for yourself.” Her mouth travelled back up to the spot behind his ear and she bit down gently, to see how he responded.

It, of course, received a pleased sound in response. 

That noise -- oh God that noise drove her crazy, she wanted him to make it again -- as a sign of approval, she bit down just a bit harder, leaving her mark for the world, including any New York pretty girls who thought they could move in on her man, to see. 

Jess felt a shiver go down his spine. “Fuck, Rory...” he all but whined. 

Her hands travelled up his back, dragging his tshirt upwards. “Off,” she demanded huskily.

He sat up momentarily to quickly take off and toss his shirt away before flipping their positions so Rory was now on top. 

Rory could not hold back her gasp as she finally, finally got to see Jess’ body. While she wasn’t surprised to find a few tattoos, including the Mariano family crest, she was surprised to find scars, standing out pale against his olive skin. Reverently, she ran a finger along a particularly nasty looking one. “What happened?” she asked quietly. Her eyes met his gently.

Words intersected that scar and joined with another: ‘The world breaks everyone, and afterward, many are strong at the broken places.’ --Ernest Hemingway 

Jess paused before speaking. “That was a stab wound and the one it joins up with is from a gunshot wound.” he couldn’t meet her eyes. 

“Jess,” she said quietly, doing her best to guide his gaze back to hers. “What’s wrong?”

Jess bit his lip, “They’re...ugly...” he said rather helplessly. 

Rory kissed his cheek and then his jaw and his neck. “No they aren’t. There is not a single centimeter of you that is ugly.” She kissed a scratch on top of his shoulder, and then what looked like another old bullet wound on the front of his shoulder. “Be proud of your scars Jess, they mean you’ve survived.” Her mouth was warm as she pressed it to the next scar down. 

Jess’ eyes fluttered closed as Rory kissed each scar; it sent little jolts of electricity through his body and made him even harder (if that was possible.) He was helpless to hold back the breathy moans that escaped him each time she kissed a new place. 

When she reached the waistband of his jeans, she teased him with hot, open mouthed kisses pressed lightly to the skin directly above.

Jess’ back arched off the bed a little and he lapsed into Italian. “Cazzo! Rory, si stuzzicare sporco.”

“Resorted to Italian, huh?” Rory asked playfully. Her fingers toyed with the button of his jeans.

Jess leaned on his elbows and gave her a pointed look, as if to say ‘It’s your fault.’ 

Rory grinned devilishly. She was just running on instinct at this point but she was rather enjoying teasing him, making him moan and whine and curse at her in Italian.

Jess caressed her cheek and tilted her chin up to get her to look at him. “Have you ever...” He gestured vaguely downward. “...before?”

Rory laughed and shook her head. “They call me Mary at school. I’ll give you three guesses as to what they mean by that, but you probably won’t need them all.” She tilted her head and considered. “Also, just say it. No I’ve never given a blowjob.”

“I didn’t know they still used that expression... Anyway, I can guide you through it, but it’s up to you, not going to force you...” He brushed a stray piece of hair from her face. 

In response, Rory grinned and her fingers deftly popped open his jeans.

Jess lifted his hips up off the mattress so that she could tug them off. 

Quickly, Rory did just that, her face flushing a little.

“You okay?” Jess asked softly. 

Rory nodded, and then looked up at him. “Yeah.”

Jess momentarily pulled her up for a kiss, “You should ditch the tshirt.”

Rory raised an eyebrow.

“Rory I have on less clothes than you, you’re basically fully clothed.” 

She considered for a second and then whipped her tshirt over her head and shook her head to rearrange her hair so it fell forward ever so slightly. “Better?”

“Much better.” Jess smiled appreciatively. 

Rory blushed and dropped a quick kiss on his lips. 

Jess deepened the kiss again and decided at the last second, that Rory should be the one to go first. He gently flipped their positions so he was back on top again and proceeded to trail kisses down her jawline to her neck, shoulders, and worked his way lower. 

“Uh, Jess?” Rory asked, her voice wobbly.

“Mhm?” Jess paused. 

“W-what are you doing?” Her voice was quiet, and she sounded unsure of herself.

Jess caressed her cheek, “I can stop, if you want me too...but I was planning on getting you off.” 

Rory’s breath hitched just a bit. “B-but…” She swallowed hard. “I was gonna --”

“After.” Jess pressed a kiss to one of the many marks he’d just made. 

Her breath caught in her throat and she could have sworn the world stopped spinning. “Jess,” she moaned.

He moved on to kiss another. “I can always stop…” he teased. 

“No!” she protested hastily.

Jess responded by running a finger along the edge of the boxers, as he quite systematically trailed kisses down to her hips. 

Rory squirmed, keyed up by the gentle teasing. “Mm.”

Jess then proceeded to gently part her legs, glancing up to make sure she was still okay. 

Her head was surrounded by the splay of her dark hair, eyes closed and mouth slightly open as she fought to control her breathing.

Jess kissed her just as he slid a hand down to start rubbing her through the rather thin fabric of the boxers. 

She gasped into the kiss, her hips pressing upwards into his hand. With a groan she bit his lip gently, her hands working back into his hair.

Jess nipped at her lips in between kissing her; his hand didn’t let up either. 

Rory could feel delicious tension curling up in her gut as Jess’ hand tormented her. Pulling away from the kiss, she buried her face in his shoulder, her breath getting noticeably faster.

Jess took that as a sign to get on with things so to speak. He tugged the boxers down and tossed them off the side of the bed. 

Pressing a somewhat desperate kiss to his neck, Rory felt her breath hitch again. “Jess,” she whispered.  
Jess slid down the bed till he was perfectly positioned between her legs, not pausing at all before he started to trail kisses and nips along her inner thighs. 

Rory whined and tried shifting her hips to return his attention to where she very desperately wanted it. No, needed it.

Jess used his hands to hold her hips down as he kept up the teasing for a few more moments. When he was satisfied, he slid a finger into her all while making sure to gage her reactions. 

Her gasp was loud and slightly ragged as one hand tugged at his hair, the other covering her mouth in slight embarrassment. 

“Rory, I want to hear you.” Jess slid his finger back out and in again, setting a somewhat slow, teasing pace. 

With a groan, Rory moved her hand to grasp at the sheets, her hips pressing downwards in an attempt to stop Jess pulling his finger back, muscles Rory had never used before tensing and grasping at it.

Jess used his thumb to rub her clit as he finger fucked her, upping the pace a bit. 

With an inarticulate little cry of pleasure, Rory’s grip on his hair tightened to an almost painful intensity. “Oh my God,” she moaned.

Jess couldn’t help but moan either when Rory tugged at his hair; he always did like it a bit rough. He slipped his finger out of her only to add a second moments later. 

Rory rolled her hips, and whimpered. “Jess, please.” Her voice was whiny and desperate, needy.

Jess started moving his fingers again, occasionally rubbing her clit at the same time. 

“Fuck…” The curse word slipped from Rory’s mouth before she could reel it back in.

Jess’s head jerked up and he caught her eye, he proceeded to grin shamelessly. 

That shameless grin pushed Rory right over the edge, and she lost her breathe as felt the world explode. Finding her voice, she managed a hazy sounding, “Jess…”

Jess gently slid his fingers from her and wiped them on the sheets. He then kissed her quite sweetly. 

Gently, Rory wrapped her arms around his neck and returned the kiss, her eyes drifting closed as she enjoyed the feel of his body against hers.

Jess pressed as close to her as possible and tangled his fingers in her hair once more. He was unbelievably hard, and it was starting to feel uncomfortable. 

Softly, her fingertips gliding across his skin, Rory trailed one hand down his chest. “You have the patience of a saint,” she said gently.

Jess shivered at her touch, “Not for long…” he sounded pretty wrecked already. 

Her hand landed on his hip and she danced a finger or two along the line of his pelvis. “You still have it in you to walk me through it?”

“Fuck, yes.” Jess grabbed the bottle of lube from his night table and handed it to her; then slid out of his boxers. 

Rory looked and felt slightly nervous but she took comfort in the fact that Jess, her Jess, was the one she was doing this with. Gently, she grabbed his hand and pressed a kiss to the palm of it.

“Okay, first put a bit of that on your hand, then you’ll do the same to me. Going at it dry doesn’t feel all that great.” 

Rory nodded and popped the cap of the bottle open, squeezing what seemed to be a decent amount into her hand. Gently, she closed her hand into a fist, spreading the lube around her hand and warming it up to something less shocking to the system.

Jess placed one of his hands over hers and guided it to his cock; he showed her how to grip and then guided her hand up and down. 

For a moment, Rory let him leave his hand gently around hers. When she felt confident enough in what she was doing, she used her free hand to bat his hand away and then pull him in for a kiss.

Jess kissed her like it’d be his last, moaning every so often, louder and more needy each time it happened.  
Rory enjoyed the effect she had on him, liked that it was her hands and mouth and body that made him moan needily. In a moment of pure instinct, she let go of his cock and gently traced the head of it with a fingertip, her nail ghosting across the skin.

“Cazzo!--Merda, Rory!” Jess’ hips arched off the mattress a bit; he was close. 

With a grin, she trailed her finger around the tip of his cock once more and then down the underside.

Barely a second later, Jess came, cursing under his breath as he did so. “God, Rory…” Jess managed to say, voice rough. His hair was messed up and he had just about as many marks as Rory did.

Pleased, she kissed her way up his neck and jaw to his mouth, pressing a very soft kiss to the corner of his lips.  
Jess made a soft pleased sound in return. 

With a slight shiver, Rory curled into Jess’ side, her head fitting into the crook of his neck perfectly.

“As much as I don’t want to move, it’s starting to dry and it feels pretty gross.” Jess laughed a bit and sat up. He kissed her cheek before walking into the bathroom to clean up. He returned less than a minute later. 

Rory had already moved under the covers, chilly and tired but still pretty wide awake.

Jess came back and got under the covers and pulled her into his arms. 

Snuggling into his side, Rory yawned and then giggled as her stomach rumbled loudly. “Well that’s one way to ruin the moment,” she giggled.

Jess laughed and pressed a kiss to her shoulder. “I can get you a snack if you want?” 

Rory looked up at him, blinking once or twice. “And a glass of water?” she asked hopefully.

“Sure.” He got up again and headed to the kitchen. He grabbed a bag of Doritos from the pantry and a bottle of water and a coke for himself from the fridge. He was back in less than two minutes. 

Rory sat up, rearranging the pillows so that they could comfortably lean against the headboard, pulling the blankets up with her to stay warm.

Jess handed her the bottle of water and Doritos before he got comfortable. He grabbed the remote from his night table and pressed the top button, moments later a TV descended from the ceiling. 

Rory squealed a little as the TV descended. “That is so cool!” she said excitedly. Jess turned it on and clicked over to the movie channels, he lit up when he noticed Almost Famous was one of the choices. 

Rory twisted the cap off of her water. “What’s on?”

“Almost Famous.” Jess tried not to look too excited. 

Rory leaned back against the headboard and took a sip of her water. “Huh,” she said noncommittally.  
Jess blinked at her lack of reaction. “It’s good?” 

“It’s fine,” Rory shrugged.

Jess happily pressed play and got comfy. He grabbed his coke from the table and took a sip. 

“You’re gonna be up all night,” Rory said teasingly.

Jess laughed. “Not likely.” 

Rory raised an eyebrow. “The caffeine won’t --” Rory froze as she heard her phone ringing. “Oh no,” she breathed, color draining from her face. Immediately she was up and racing for the phone tucked into her jeans pocket.

“Rory?” Jess asked, concern lacing his voice. 

Grabbing her phone, Rory started truly panicking. “It’s my mom,” she said, her voice cracking a bit in fear.

“Rory, take a deep breath and just answer. She probably just wants to say goodnight. 

Rory nodded and took a deep breath, opening the phone and pressing it to her ear. “Hello?”

“Rory, thank God. Why didn’t you answer any of my text messages?” Lorelai asked, concerned.

“Sorry mom! I had it on vibrate and couldn’t hear it going off. Paris never stops talking. I’m surprised she has a voice left.” 

Lorelai hmpfed. “Slip something into her drink and go to bed. It’s late, and break or no, being up all night on a school night is not a good idea.” Lorelai’s voice gentled. “I love you, Rory. You know that right?”

Rory was a bit thrown by Lorelai’s question. “Of course I know that!, I love you too. You’re my best friend.” 

Lorelai chuckled. “Well that’s a pretty high compliment. Anyway, I just wanted to make sure you hadn’t killed anyone yet and remind you that whatever Paris says, you need sleep, okay? Goodnight.”

“Okay, night mom.” Rory giggled. 

Shutting the phone, Rory slipped it back into the pocket of her jeans and muttered, “Thank God.”

“Rory….” Jess paused before continuing. “I thought that your mom knew where you were...” 

Rory blushed and couldn’t turn around to face him. “She doesn’t,” she said, so quietly there was almost no chance he’d heard her.

“Wait, does she even know about me?” He guided her back to the bed. 

She shook her head and looked down as her blush deepened. “Not yet. I just...I haven’t figured out how to tell her yet and especially now that I know you’re part of the mob.” Rory started babbling. “Please don’t be mad. I keep trying and I just can’t get the words out. And if she knew, she’d never let me come visit you here, by myself, and then we wouldn’t have been able to, you know.”

“Rory, breathe, I’m not mad.” He pulled her into his arms and hugged her close.

Gratefully, Rory wrapped her arms around his waist and buried her face in his chest, taking deep breaths and reigning in her wild train of thought.

“I’ll help you tell her, I’ll drive down to Stars Hollow for a day. Just, you know she can’t know about my “job” right?” Jess played with her hair and rubbed her back.

Rory looked up at him. “If you say so.” She took a shaky breath. “But what are we going to tell her?”

“The truth, with a few minor alterations. Leaving out you visiting here alone and maybe tweaking how we first met.” 

Rory nodded. “And I imagine you’re just going to say you work for your dad?”

“Yep. Finance.” He made a face. 

“Is it that bad a thought?”

“No, I just hate math.” 

Rory gently slapped his arm. “Goof.”

Jess laughed. “Come on, let’s watch the movie then we can go to sleep.” 

“That sounds nice,” Rory said drowsily.

Jess pulled the covers up around them and pressed play. 

Sleepily, Rory curled into his side, one arm draped across his stomach. “Mm.”  
\----  
At some point during the movie, both Jess and Rory fell asleep; and around 3am Jess woke up and jumped out of bed, heart pounding, breathing ragged. He’d forgotten to put the music on.

Rory stirred gently and quietly called his name when she discovered he was missing from the bed. “Jess?”

“F-fuck..sorry, I didn’t mean to wake you.” His voice sounded...wrong. He shakily ran a hand through his hair. 

Rory crawled across the bed to him, grabbing his hands with both of hers, pressing the palm of one of his hands to her heart. “Focus on my heartbeat. Match your breathing to it.” Her heartbeat, still very slow, thudded solidly in her chest.

Jess closed his eyes and focused on matching his breathing to hers. It took a couple of minutes for him to calm down again. 

When she could sense that he wouldn’t spook, she placed the hand not holding his palm to her heart against his cheek. “That must have been one hell of a nightmare,” she murmured.

Jess rested his forehead against her shoulder. “...Happens most nights, usually if I forget to turn on my music.” When he spoke, his voice was barely above a whisper. 

She moved her hand from his cheek to his hair, brushing it off of his clammy neck and forehead with gentle fingers. “Wanna talk about it? Or do you wanna turn the music on and go back to bed?”

“Second one,” he mumbled. 

“Okay,” Rory said lovingly. “Where are the controls for the music?”

“I can do it.” Jess kissed her forehead; he then walked over to the stereo and turned it on, popping in a Clash CD. He made sure it was at a reasonable volume before he got back in bed. 

Rory folded the covers back and held out a hand to him, pulling him into bed.

He took it and scooted closer to her. 

Gently, Rory snuggled into him, one leg wrapped around his as a sort of anchor. With a kiss to the underside of his jaw, Rory yawned and was almost instantly back in a serene sleep.

Jess was very much content with their new sleeping position and relaxed completely; he was asleep in mere moments.  
\----  
Rory next woke to sun peeking around the curtains, trying in vain to reach the bed. Snuggling closer to Jess, she was content to stay put for a bit, since the clock on the bedside table informed her that it was only seven-thirty.

Jess rolled over and looked at her with the cutest sleepy expression.

“Morning,” Rory whispered happily.

Jess responded by nuzzling against her shoulder. 

“Did you get some decent sleep?”

“Much better than I usually do.” He mumbled, still sleepy. 

Rory grinned. “You’re still half asleep. Go back to sleep.”

Jess cuddled closer and did just that. With a gentle smile, Rory settled in to doze and put together a mental plan for the day. She’d told her mom she’d be home in time for dinner, so at latest, she could leave New York -- could leave Jess -- at about two and make it back to Stars Hollow by about six. And should her buses be delayed, she’d call and say the project had taken longer than expected.  
\----  
Jess woke again around 9:45 and stretched. He tugged on a pair of sweatpants and made his way to the kitchen to start breakfast.

Fifteen minutes later, the smell of food roused Rory from sleep, and she grabbed the clothes she’d put on after her shower the night before, pulling them on before padding down the hall to the kitchen.

Jess had breakfast just about finished when she walked in. He’d made chocolate chip pancakes and coffee. 

“It smells wonderful,” Rory said as she entered the kitchen, reaching for one of the mugs of coffee sitting on the counter next to the pot.

Jess flashed a smile her way as he finished dishing them up. 

Rory smiled and looked down just a bit as she sat down at the table, content to sit and watch Jess finish cooking.

Jess brought their plates over and the extra pancakes too. 

Rory took her plate with a grin. “You’re going to spoil me, Mariano.”

Jess grinned. “Damn right, I am.” 

Rory bit her lip and realized, somewhat surprisingly, that she was fighting the urge to sniffle and cry a bit. “Oh my gosh.”

“Rory?” Jess took her hand, concerned.

Rory used her other hand to wipe at her eyes. “I’m fine, I swear. Just...sort of overwhelmed, I guess. Because no one’s ever flat out said they were going to spoil me, especially not someone I’m dating.”

Jess got up and hugged her close. “It’s okay...I just...I...” he bit his lip. Was it too soon to say he loved her?

She looked up at him, one hand still brushing away tears. “What?”

“I...I love you...” The words came out shakier than he’d expected them too. 

Rory’s eyes got very wide, and her lip trembled for a second before she threw her arms around his neck and whispered, “I love you too.”

Jess felt so relieved to hear her say it back. He hugged her tight and kissed the top of her head.

Rory’s heart beat a quick staccato against her rib cage. She couldn’t believe they’d actually ‘fessed up to each other, that it had been so easy to say that within seconds. Nothing like when Dean had said it….

Jess kissed her cheek before he stood. “We should eat before they get cold.”

Rory laughed and nodded, tears still pooling in the corners of her eyes. “Indeed. It would be a shame if such wonderful looking pancakes didn’t get eaten.”

Jess smiled and poured syrup all over his before digging in. 

Rory put a pat of butter between her pancakes and gave it a bit to melt, enjoying the view of Jess digging into his food before she began eating her own.  
\----  
By the time breakfast ended, all the pancakes had been consumed and a good portion of the coffee. Rory nursed her third mug of coffee as Jess cleaned up. He’d refused to let her help, so she sat at the table, feet tucked up in the chair with her as she watched him clean up the kitchen. It took him a good 10 or so minutes for cleanup. By the time he had finished, Rory was two-thirds of the way through her coffee and the clock was showing a time of close to eleven. “I don’t want to go home,” Rory said softly into her coffee.

Jess walked over to her. “I don’t want you to leave either.”

“But I have to,” Rory said, voicing the thought both of them had left hanging in silence.

Jess silenced all other words or thoughts she may have had with a kiss. He gently took the mug from her hands and set it back onto the table without breaking the kiss. 

For a little bit, Rory was content to just let him kiss her, but eventually reality nagged at her. “Jess,” she said quietly, her tone laced with a firm sadness she hated hearing there.

Jess sighed and stood up. “Alright, come on, let’s go get dressed.” 

Rory smiled sadly. “Sorry.”

“Nothing to be sorry for.” He offered her his hand. 

Accepting the hand, Rory unfolded from her chair and followed him back towards the bedroom. “I love you,” she whispered as they made their way.

“Love you too, Booktease.” 

She shoved him playfully with her shoulder and suddenly the mood was a lot lighter. Rory’s imminent departure no longer felt like a death sentence.

Jess changed into black jeans, a Metallica tshirt and grabbed his leather jacket. He spent some time in front of the bathroom mirror fixing his hair. 

Rory, who managed to shower in the time it took him to dress and work on his hair, laughed as she took a towel to her hair. “Wow, Jess. Elegantly disheveled much?”

Jess stuck his tongue out at her. “It’s an art.” he said slightly sarcastically, but soon smiled.

Rory, for her part, grinned and stole a comb to take the tangles out of her hair before braiding it quickly. With a quick kiss to his cheek, she walked past him to the bedroom where her things were waiting for her to pull them on.

Jess pulled his socks and shoes on and pocketed his phone, keys, and wallet. He made his way to the safe and tucked one of his guns in the inside pocket of his leather jacket. 

Rory, who was buttoning up her sweater, pointedly ignored the gun. She was, honestly, okay with who Jess was. But guns made her uneasy and it would be easier to act like it wasn’t there if she just ignored it from the start.

“Ready?” Jess locked the safe back and stood up. 

Rory nodded and grabbed her purse, looking around to make sure she had everything. The last thing she needed was to leave something behind and have to wait until Jess came to visit next week to get it back. Jess took her hand and led her out; he locked the door behind them and pressed the elevator button. It dinged and opened a moment later.Rory stepped into the elevator and used her free hand to press the button for the ground floor. When the elevator stopped Jess led them down a few steps and out the door to the garage where his car was. He didn’t want her riding the bus again. 

“Where are we going?” Rory asked, trailing after him.

“I’m going to drive you back.” Jess stopped in front of a gorgeous midnight blue, two door, 1969 Ford Thunderbird. 

“That’s your car?” Rory asked quietly. “You better not be planning on driving me all the way to Stars Hollow because there is no way you’ll fly under the radar with this thing.”

Jess smirked. “No, I’m going to drop you off in Hartford.” 

Rory released the breath she hadn’t realized she was holding. “Good. And wipe that smirk off of your face, Mariano.”

“Mhm.” Jess made no move to do that as he unlocked the doors and got in the driver’s seat.

Rory hmpfed, eerily similar to her mother, and climbed into the passenger’s seat, dropping her purse onto the floorboard by her feet.

Jess started the car and it roared to life, he pulled out of the parking space and exited onto the street. “Press play for me? I’ve got a CD in.” 

“Sure,” Rory said, poking the button in question. The Distillers blared from the speakers; Jess reached over and turned it down to a more reasonable level. Once the volume was down at a decent level, Rory grinned appreciatively. “At least you have good taste in music, even if your taste in literature is questionable.”

Jess rolled his eyes. “I have great taste in literature.” 

“Hemingway,” Rory responded. “Seriously questionable.”

“I think you mean Rand.” 

“No, I definitely meant Hemingway, Mariano.”

“Huh. Cause I think Rand makes far more sense, Gilmore.” Their bantering continued for a while, playfully teasing the other about their preferences.  
\----  
Somewhere around the halfway point, Rory interrupted the teasing to ask, “Mind finding a place to pull off? I need a restroom.”

Jess nodded and pulled off at a gas station/rest stop. He went ahead and filled the car up too.  
As Rory came out, she saw Jess leaning against the car, two girls about her age standing a couple of feet away. They were too far away for Rory to make out anything other than tone, but it was obvious from their body language that they were flirting. Jess, for his part, seemed cool as a cucumber, eyes hidden behind sunglasses, barely talking. As Rory drew nearer, she looked pointedly between Jess and the two girls. “We should head out, love. Got a ways to go yet.” Jess pulled her close and kissed rather passionately. He had no interest in either of the two girls. 

Rory returned the kiss and grinned. Still grinning, she turned to look at the other two. “Is there something I can help you guys with?” she asked sweetly  
.  
The girls huffed and stalked away. Jess couldn’t help but laugh. 

“That’s what they get for hitting up a guy with obvious hickeys.”

Jess laughed a bit harder as he walked back to his side of the car. “Love you.” He grinned. 

“Love you, too,” Rory responded over the top of the car before they climbed in.

They were off again in a matter of moments. Jess gunned the engine and they sped off. 

Before Rory could come to terms with her time with Jess almost being up, they were pulling into the Hartford bus station.  
\----  
Jess turned the car off for their goodbyes.

“Jess,” Rory said quietly. “I...hrm.”

“You what?” Jess didn’t quite catch that last part. 

“Sorry,” Rory said with a blush. “My brain tried to send like five different words to my mouth at once.”

Jess smiled. “It’s okay.” He quieted a moment. “I’ll miss you...”

Rory, rather than saying anything, leaned over and pulled his face to hers for a kiss.

Jess kissed her with everything he had. 

Breathless, Rory pulled away and frowned. “I wish I didn’t have to go...Monday feels so far away…”

“Texting, phone calls, we’ll manage...mostly...” He kissed her one last time. 

Sadly, Rory grabbed her purse and opened the door. “I’ll text you when I get home and you mister better do the same.”

“I will...Rory?” 

“Yeah?”

“Love you.”

Rory grinned. “Love you too.” Rory got out of the car and gave him one last look before she hurried over to board her bus. Across the street, Dean Forester couldn’t believe what he was seeing. Who the hell was that? The guy she dumped him for? And where had he and Rory been? Taking note of the New York state plates on the car, Dean shook his head and continued walking. He’d get to the bottom of it soon enough.  
Rory boarded the bus, waving sadly to Jess who was still sitting in the parking lot. It was going to be a long week.

**Notes for the Chapter:**

> Also note, neither PrincessaKyla or I speak Italian, so we've done our best to translate:  
> Cazzo, si stuzzicare sporco-- Fuck, you filthy/dirty tease.  
> Cazzo--Fuck  
> Merda--Shit


	7. Dear Father

**Notes for the Chapter:**

> This was honestly one of my fave chapters to write. Quite a bit of Jess feels too.

[Back in SH, meet at Luke’s? -R] 

Lorelai considered the text sitting on her screen. [Give me ten to wrap things up and I’ll be there, Loinfruit. -L]

[Ok :) -R]

Rory headed to Luke’s to get them a table, as she walked she sent Jess a text. [Home now. Miss you. -R] she didn’t expect a response for a few hours. Lorelai, true to her word, breezed into Luke’s relatively soon after, her giant smile aimed solely at Rory. “Hey kiddo! Got your project finished I assume?”

“Done and ready to hand in!” Luke came over then and filled two cups of coffee. 

“Thank you,” Lorelai told Luke with a smile. He grumbled at her a bit but smiled just a little and as he walked away, Lorelai turned her grin back to Rory. “It was so quiet last night. Too quiet. I ordered a stripper and some singing telegrams but all that ever showed was pizza.”

Rory giggled. “I missed you too. We can always do something tonight? I finished all my homework.” Rory took a big sip of her coffee. 

“I think that is a wonderful idea,” Lorelai responded. “Maybe we can order strippers again.”Luke gave Lorelai an odd look as he refilled their cups, Lorelai simply grinned in response. 

Rory almost choked from laughing. “Okay, I’m gonna go see Lane, I’ll be home in a bit, and no strippers!” 

Rory kissed her cheek and headed out. It took her maybe three minutes to get to Lane’s, partially due to excitement. Rory walked up the steps and made her way inside. “Lane?” 

“Rory!” Lane responded excitedly. “You better be coming to tell me details!”

Rory headed into the kitchen where Lane was finishing up the dishes. “Of course! I have so much to tell too, Lane...you’re not gonna believe it!” Rory grinned. 

Lane grinned and raised an eyebrow. “Do tell.”

“Upstairs?” Rory definitely couldn’t risk someone overhearing what she was going to say.

“Sure. Mom’s --” Lane was cut off by a stream of very loud haggling. “Well she’s here but she’s busy, so she won’t bother us.”

Rory nodded and followed Lane upstairs; only once they were safely in the closet oasis did Rory begin. “Okay, where should I start?”

“Um, at the beginning,” Lane said impatiently.

“Lane. He lives in a penthouse. When the taxi pulled up in front of the building I about died! There was a doorman! And they call Jess Mr. Mariano.” 

Lane squealed a giggle and motioned her on. “Oh my God.”

“The elevator dropped me in his private hallway and, of course he was surprised to see me when he opened the door. But his place is so cool! He has a gorgeous view of the city. And he has a wall bookcase in his bedroom, and a giant bed and his bathroom. Lane. There’s a jacuzzi and a shower! And his closet is like a mini room! Plus the decor...and the kitchen…” Rory finally had to catch her breath. 

“It sounds amazing,” Lane said, her grin fighting to spread.

“And he cooks! He made me dinner! With red wine and everything!” 

Lane’s eyebrows flew upwards. “Wine? Rory, you drank alcohol with him?”

Rory squirmed a bit. “Just a glass...he’s Italian, he has it with dinner every night.” 

Lane shook her head a bit. “Okay. Anyway, go on!”

“Then after..we moved to the sofa.” Rory blushed a bit. “We started kissing but that turned into something more rather quick...probably because I straddled his lap...” 

Lane’s jaw dropped and she sat in stunned silence. “Woah…” she finally managed.

“We uh...we didn’t exactly stop there...” Rory bit her lip. “He uh...carried me to his bedroom while we continued to kiss.” 

Lane sat back in shock. “Like actually carried you?”

Rory nodded, blushing and smiling. 

Lane nodded, impressed. “And should I assume there was more kissing or...more...in the bedroom?”

Rory wiggled a bit. “We did some stuff...like...not full out sex, but we did things of the sexual nature.” Rory tugged her shirt collar way down to show off one of the marks he’d left, blushing a bit more.

Lane leaned forward and blinked. A lot. “How did your mom not see that?”

“I’m very good at hiding. And uhm...there are others, kind of all over.” Rory went cherry red. 

“Wow. Rory, are you sure you aren’t moving too fast? I mean this is way further than you went with Dean.”

“But I didn’t love Dean. And...and I love Jess. He loves me too -- actually, he said it first.” 

Lane shook her head in disbelief. “Rory I can’t believe it. It’s like being in a storybook.”

“You should see his car too...Lane, my mom would freak. It’s this hot-rod-gorgeous midnight blue classic Thunderbird.” 

“He’s totally the type,” Lane said with a grin. “And you’re so lucky.”

Rory sighed dreamily, “He’s...perfect.”

“Sure sounds like it.” Lane reached over and grabbed Rory’s hand. “Are you happy?”

“Happier than I think I’ve ever been.” 

Face stretched in a smile, Lane said, “Good.”

They chatted a bit longer before Rory had to go back home.

Giving her a quick hug at the door, Lane said, “Just be careful okay?”

“I will.” Rory smiled at her before she headed home. Nothing could bring her down. 

Except, maybe, the prospect of introducing Jess to her mother. Rory wouldn’t think about that now -- she and Lorelai had a fun girls night planned.   
\----  
Jess Mariano had made great time leaving New York and would be pulling into Stars Hollow momentarily. He turned down his radio a bit as he made it to the town line but it could still be heard, what with his windows down. It was certainly a small place to say the least. It looked like it popped right out of a story book. And apparently the townspeople didn’t get a lot of out-of-towners considering the looks he was getting, certainly none with a classic hot rod. Jess noticed Rory’s bus docking at the same time the local high school seemed to be letting out. He pulled up and parked on the side of the street a few feet away, turned off the radio and shut the engine off before getting out. Jess got even more looks once he stepped out of the car. He was wearing black boots, dark wash jeans with a black belt, a long sleeve white button up dress shirt complete with black tie and silver tie pin. What really set the look off was his more formal leather jacket. He looked equally business and casual rebel. He certainly turned some heads, not that it mattered in the least to him; he was focused on Rory. She was getting off the bus just as he was walking over. “Rory.” Jess grinned, now less than three feet away. 

Startled, Rory turned to see who was calling her name. A grin spreading across her face, she launched herself across the distance into his arms. “Jess!!”

Jess grinned and pulled her close. “I’m going to kiss you now.” He proceeded to do just that too, making sure it was quite the passionate display. After all, if everyone was gonna stare; why not give them a show? 

Rory kissed him for a few moments before pulling away and grinning. “Well that was a pleasant surprise.”

“That was my plan.” Jess slid his arm around her waist.

A few feet away, Dean was staring in a mixture of shock and fury. That was the same car he’d seen Rory get out of last week! It all made sense now; he was also banking on the fact that Lorelai probably knew nothing. Well, he’d fix that. Dean stormed off towards the Dragonfly Inn. 

On the other side of the street, Taylor, Miss Patty and Babette were in equally a state of shock. “Mhm...well isn’t he a looker.” Miss Patty grinned. “Always knew Rory was a bit more like Lorelai than she let on.”

“It’s disgraceful, that’s what it is! She has no business with a hooligan like that boy!” Taylor huffed. “And… and that display!” He turned and quickly headed back to his shop. 

Miss Patty and Babette shared a laugh before they headed to Luke’s. 

Rory glanced around and sighed. “Well here’s hoping no one tells Mom before we do…”

“Should we head over there? Or did you want to meet her at your house?” 

Rory’s phone buzzed before she could answer and she flipped it open to see a text from her mother. [Home. Now. I’ll meet you there. -L] “Home,” Rory said, her face and voice pinched.

Jess noticed of course. “Shit...she knows doesn’t she?” Jess slid his arm around her waist as they started off towards the Crap Shack. 

Rory nodded. “I’d be willing to bet my ex is involved somehow…” she muttered.

Jess tensed. “If that’s true, he’ll get a fist in his face,” he mumbled.

“He’s not worth it,” Rory said quietly. “He’s really not.” Looking around, she noticed that people were doing their best to stop staring. “Ohh great….”

“Ignore them.” Jess kissed the top of her forehead. 

“Easy for you to say, you get to leave,” Rory muttered darkly.

“Rory.” Jess said, bit of a warning tone. “You know I’d stay if I could.”

“I’m not holding it against you. I’m envious. I was the subject of the stares a week or two ago when I broke up with Dean, and now I’m the subject again. And the chances of someone giving them a bigger piece of gossip any time soon are slim.”

“That honestly really sucks...but, I can visit more now? It’s not that bad of a drive, and what with my Dad giving more of a free reign.” They were nearly to her street. 

Rory swallowed hard. “Maybe. First we have to see what Mom says…”

“Rory, I’m not just going to not see you. Regardless of what she says. I’ll drive down here every day if that’s what it takes.” 

Rory looked up at him and tried to smile at him. It came out more of a funny sort of grimace. “I know...I just...she’s my best friend and I don’t want to...to alienate her.”

Jess nodded. “We’ll figure something out.” 

Rory swallowed hard again and led him up the steps to the front door. “Here we go…” Jess took her hand and followed her inside.

Inside, Lorelai stood waiting in the entryway. “Couch,” she said, pointing imperiously. 

Rory and Jess sat down on the couch, Jess didn’t let go of her hand.

“Now will someone,” Lorelai began angrily. “Explain to me what the hell is going on? I’m at work and all of a sudden I get a call from Dean, of all people, telling me that not only is Rory with some very troublesome looking guy in the middle of town, but that he’d seen her getting out of his car in Hartford last Wednesday morning. What the hell, Rory?”

“I knew it! Dean is such a jerk!” Rory blurted out. “Jess came here today so that he and I could talk to you about us and Dean goes and ruins everything!” 

Lorelai blinked and crossed her arms. “And why didn’t you tell me before now that he was coming today?”

Rory bit her lip, trying to figure out what to say. “I didn’t think you’d be okay with it, and I didn’t want you to make me feel bad about it when I’ve been so happy...but that was wrong, I should have told you.” Rory’s eyes watered a bit, and Jess gave her hand a squeeze.

“You’re damn right you should have!” Lorelai took a deep breath and tried to calm down a bit. “And why on Earth would you think I wouldn’t be okay with it? I literally know nothing about…” She gestured helplessly. “Sorry, but what’s your name again?”

“Jess Mariano, Ms. Gilmore.” 

“Thank you. I don’t even know anything about Jess so how on Earth could I be okay with this or not?”

“Well, that’s what today was for? So I could introduce you to him and you could be okay.” Rory managed a bit ineloquently. 

Lorelai squinched her eyes shut and pressed her fingertips to her temples. “I just don’t understand where this is all coming from. I mean one minute you’re breaking up with Dean and don’t love him and the next you’re bringing home a guy to meet me?”

Rory squirmed. “I met Jess at Phantom of the Opera. His seat was next to mine. We talked about books and music….things that Dean and I could never connect on.” 

Lorelai sighed and steepled her fingers together in front of her mouth. “Okay… Makes sense. But this seems awfully fast, you guys. I mean that was what, two weeks ago?”

“We’re not moving too fast, we text and call each other and we’ve hung out after school in Hartford... but you had to meet him at some point? And he drove all the way from New York...” Rory wasn’t sure what more to say. 

Lorelai tipped her head and held up her hands. “I’m not...I’m not gonna police the relationship, but seriously Rory. Don’t be me.”

Rory’s head jerked up, expression of a deer caught in headlights. “Mom, y-you know that I wouldn’t...” 

Lorelai’s eyes widened. “You didn’t!”

“No! I didn’t do that!” 

“But you did something!”

Rory made a distressed sound. 

Lorelai’s eyes squinched shut and she held up both index fingers. “No you know what? We’re not gonna talk about it. Both of you, out. Go to Luke’s. I’m going to wrap my head around this before I do something I regret.”

Rory fought back tears and stood up, pulling Jess along with her. 

“Rory,” Lorelai said softly. “Just...Let me wrap my head around it okay? I’m really more shocked and hurt than anything else. But right now, the guy pegging my daughter is looking like a really good punching bag.”

Rory’s eyes shot wide. “We’re gonna go!” She all but dragged Jess out of the house.

Lorelai collapsed on the couch when they were gone. “Why did she have to turn out like me?” she asked the empty room.  
\----  
“Rory, look at me.” Jess stopped halfway down the street and slid his arms around her.   
A single sob escaped from her throat, rough and painful sounding. “Sorry,” she sniffled. “She just...and I got...and oh my god.”

“Shhh, hey, Rory, things’ll be okay.” He rubbed her back and ran his fingers through her hair. 

She nodded and did her best to quiet her sniffles. “I know, I just...She had me at sixteen and I know she’s seeing all of my future go down the drain now that she thinks we went all the way.”

“She’ll come around, she loves you Rory, you said yourself you guys are best friends. And I won’t let anything happen to you. We’ll be careful.” Jess felt his heart tug painfully, he hated seeing Rory like this; he couldn’t help but be a bit envious at their relationship though. He wished his parents gave a damn. Hell, he didn’t even know his mom. 

“I know...And at least my mom’s not gonna pull a gun on you or something.”

Jess’ body went rigid.

Rory felt her eyes go wide. “Oh my God I’m so sorry, I said that without thinking. I am so so sooo sorry, Jess. Please don’t hate me.”

Jess took a deep breath and let his eyes close before he spoke. “I’m okay, Rory, really, it’s fine. I know you didn’t mean it.” 

“Are you sure?” she asked quietly. “I’m really really sorry.”

Jess responded with a kiss. “I’m sure.” 

“Okay,” Rory said gently. “Coffee? I’m sure you must be hungry too...” 

Jess smiled but it didn’t quite reach his eyes. “Lead the way, Gilmore.” 

With a gentle smile, Rory turned and, grabbing his hand, leading him back towards the center of town. “Let’s go to Luke’s, then.”

Jess followed along beside her. “Do you go to Luke’s often?” 

“At least once a day, usually more. Best coffee in town.”

Jess nodded. “Take your coffee with an IV do you?” he teased. 

“No but Mom does,” Rory responded, deadpan.

Jess blinked. “Huh.” 

Rory giggled. “Luke threatens to cut her off all the time. Keeps telling her it’s horrible for her.”

Jess laughed a bit. “Well, that much can’t exactly be good...” He held open the door for her as they walked into the diner. 

It was, blessedly, mostly empty. Heading to the counter, Rory grinned, Jess followed along behind her. “Hey Luke.”

“Rory.” Luke smiled a bit before going back to making more coffee. 

“So I’ve got someone for you to meet,” she said, continuing.

“Oh?” Luke paused what he was doing. Jess looked up from the menu. 

“Luke Danes, meet Jess Mariano.”

Jess went rigid and looked up at Luke. Luke looked equally as tense and shocked. 

Rory, somewhere in between the two of them, looked from one to the other, confused.

“Surprising that you could take the time to come all the way out here. Shouldn’t be surprised, you’re Jimmy’s son after all.” 

Jess’s eyes darkened. “Fuck you. You don’t know shit about me Uncle Luke. Last time I checked Liz was the one that ran out on me, not the other way around.” 

Rory stood there in shocked silence. Kirk and the other patrons stared; no one dared make a noise. 

“Hey!” Luke said angrily. “That’s my sister, your mother, you’re talking about. And whatever your relationship with her, it’s separate from any relationship we might have built.”

Jess stood up. “What relationship?! She bailed! No cards, no phone calls, hell, not even a smoke signal! I. Don’t. Know. Her. And what about you? Huh? If you cared so much why didn’t I hear from you? Jimmy won’t win any father of the year awards, but at least he didn’t bail.” 

Luke pressed his lips together, raising an index finger and starting to say something before lapsing into silence for a second. “You…” He swallowed hard. “Rory, take him upstairs to my place. We need to talk.”

Jess ran a shaking hand through his hair. Rory gently took his hand and led him along. Jess went wordlessly, not really processing much at this point. Kirk rushed out the front door, no doubt to go tell the town gossips. The other patrons quickly paid and left as well. Luke, locking the door after the last person left, threw down the dish towel that had been draped over his shoulder and cursed. “Shit!” Taking a deep breath, he turned to make his way upstairs. “We messed up, Liz. We messed up royally,” he muttered.

Upstairs Jess and Rory were sitting at the kitchen table. Jess looked….a mess at best. 

“Hey,” Rory said gently, giving his hand a squeeze. “It’s gonna be fine.”

Before Jess could respond, the door opened and Luke walked in, looking slightly dejected. “Jess…”

“What?” It came out utterly void of emotion. Jess had all but shut down. 

Luke swallowed. Hard. “I’m gonna guess you never got the birthday cards I sent you. And I sincerely doubt your dad was telling me the truth when he said you were at boarding school.”

Jess’ head jerked up. “Boarding school? I go to a shitty NYC public school. What...I don’t…” Jess’ thoughts were swimming. Jimmy had been talking with his mom and Luke? All this time and he never knew? 

Luke snorted. “Figures. Your old man is a right piece-a work, ya know that?” Luke shook his head. “I sent you a birthday card every year until you were...God fourteen? Called every holiday, and weekends. I knew better than to believe he was shelling out the money to send you to boarding school. The shit bag…”

Jess let out a hollow, broken sounding laugh. This wasn’t good, he was going to lose it any second now. “Jimmy’s done a lot of shit, but I never...I thought...” Jess felt his heart speed up, breathing getting to be more erratic. 

“I think I can figure it out,” Luke said, his tone final. “God.”

Rory noticed that Jess was losing it. “Jess,” she said gently. “Breathe slowly?” She grabbed his hand and, ignoring Luke’s questioning look, held it to her chest and said, “Match your breathing to mine, Jess.” 

Jess shook his head frantically. “I...c-can’t…” 

“Jess, look at me,” Rory said, fighting desperation.

Jess stood up and started pacing; his hands were shaking badly as he ran them through his hair. “Cazzo!” He brought his fist back and punched the wall, finally losing it and began speaking frantically in Italian. 

Luke looked at Rory, clearly panicked. Rory shook her head at him.

“What’s wrong with him?” Luke asked quietly.

“He’s...we’ll let him calm down and then he can explain.”

Jess punched the wall till he was sure his hand was broke. His legs gave out beneath him and his knees hit the floor. 

Luke started towards him, eyes wide, but Rory put a hand on his arm to stop him. “Let me.”

“He’s not...he’s not okay.” Luke’s voice broke a little as he watched his nephew suffer. “I knew that bastard would mess him up…”

Rory crossed the room to kneel next to Jess, pulling him into her arms. “Jess…”

Jess leaned forward and rested his head on her shoulder, exhausted. 

“Are you ready to talk?” Rory asked very quietly, her breath warm across his ear.

“Can you just...hold me?” Jess’ voice was rough and a bit scratchy. 

“Of course,” she responded, pulling him closer. She sat back on her heels, one hand drifting upwards to brush at his hair.

Slowly, Jess let himself calm down. He focused on her heartbeat and her fingers brushing through his hair. They stayed like that for several minutes. 

Luke, looking for something to keep his hands busy, worked on making coffee as Jess let Rory hold him. Marvelling at the urge he felt to go beat the crap out of the man who’d hurt not only his sister, but his nephew, Luke instead took out his anger on the water taps.

Jess, finally calm enough, lifted his head and stood up. Looking down, he finally noticed the mess he’d made of his hand. “Shit...” 

Rory got up and led him towards the bathroom. “Luke, you have a first aid kit in here?”

“Yea, I’ll get it.” Luke abandoned the coffee pot and quickly grabbed the first aid kit, bringing it in to them. Jess was now seated on the edge of the sink. 

“Thanks Luke,” Rory said with a small smile, taking the kit and opening it to look for antiseptic and antibiotic ointment. “Jess next time try not to bust your knuckles okay?”

“Next time I’ll bust Jimmy’s face open,” Jess said under his breath. 

“Jess,” Rory said warningly. “There have to be better ways to deal with him than that. I happen to know some very effective poisons.” Her voice was almost silent, meant for Jess’ ears alone.

“I want him to suffer.” Jess responded, just as quiet. 

“Somehow, I doubt you splitting his face would do much more than make him angry.”

Jess chose not to reply. 

Rory took his silence as avoidance and sprayed the bleeding places on his hand with antiseptic. He drew his hand back a bit, hissing, “Sorry.”

“I’ve had worse.” 

“I know,” she muttered angrily. Next came the antibiotic ointment and bandages.

“Wait. What do you mean you’ve had worse?” Luke asked, concerned and not quite sure he wanted the answer. 

Rory kept silent and gave Jess a look that said, “This is your conversation.”

“Kitchen.” Jess waved his hand and hopped down from the sink. He took his tie off and shrugged out of his leather jacket. 

Rory stayed back a few seconds to repack the first aid kit while the guys went back to the kitchen.

“Coffee?” Luke offered. He dreaded this conversation.

“Please.” Jess took a seat at the table. Rory did the same about a minute later. 

A little bit later, Luke served up the coffee and sat down. “So…”

“What do you know about Jimmy? About his business?”

Luke looked at Rory. “Does she…?”

She nodded. “I know.”

Luke sighed and ran a hand down his face. “Well, it’s kind of impossible to be related, however loosely, to the biggest mob boss this side of the Mississippi and not know, now isn’t it?”

Jess sighed. Instead of replying, he unbuttoned his dress shirt and shrugged it off revealing The Mariano Family crest and all his scars. 

Luke nodded. “I knew it.”

“You’re taking this well.” Jess started to put his shirt back on. 

“Well when your ex-brother-in-law sends goons after you to make sure you stop reaching out to your nephew, it tends to set the bar high. Plus, the big freakout came when your mom got seriously involved with him…”

“Geeze...” Jess ran a hand through his hair. “Look...you both know I’ve gotta go back later today, but Luke? You need to keep Rory safe. And you need to keep tabs on her. Neither of you can call me, or text me till I get back. Do I make myself clear?” Jess spoke in a tone clearly used to command authority. 

Luke nodded, his expression grim. He knew what was coming, and he knew that Rory was about to have her world turned upside down. “You got it.”

Rory looked like she was about to protest. “Jess…” Her voice trailed off. “Fine.” Her voice and breathing were shaky.

“Rory. You are more important to me than anything or anyone, and I need to keep you safe.” Jess took her hand in his. “The second things are handled, I’ll call you, and I’ll come back.” 

She nodded, but she was obviously upset. 

A thought popped into Jess’ mind. “Stay here, I’m going to the car to get something.” He gave her a chaste kiss before he grabbed his leather coat and headed out the door. He put his tie on on the way out. 

Rory took another shaky breath and Luke caught her attention. “He’s gonna be alright, Rory.”

She looked at him. “I hope so.”

Jess came back with a small bag about 5 minutes later. He set it on the table and dug out item number one: a silver chain that had the Mariano Family crest on it in the form of a locket; it had his last name written below the crest. “Rory...” he wasn’t quite sure what to say so he simply placed it in her hand. 

Her forehead creased, and she looked up at him, slightly confused. “Jess?”

Jess actually blushed. “It’s uhm...when a boss or an heir...” Jess paused, tripping over his words. “It uhm...it means that we’re together and if anyone so much as looks at you wrong, they’ll answer to me.”   
Rory sat back heavily in her chair. “Wow…” she said quietly. Looking up at him she asked, “Another way to keep me safe?”  
Jess nodded, blush still evident. “And...for when I’m not around...so you don’t feel so alone.” Jess said that last part rather quietly.

Rory toyed with the necklace for a second before offering it to Jess. “Help me put it on?”

Jess wordlessly unclasped it and clasped it back around her neck. 

The unfamiliar weight of the metal settled on Rory’s chest and she grabbed at it with her hand, fingers cherishing this little piece of proof.

Jess kissed her cheek before he moved back to the bag. He reached in and pulled out an HK45 Tactical handgun, along with appropriate ammo. “Luke.”

“Jess!” Rory objected.

“No, no. He’s doing what he has to,” Luke said knowingly. “He’s his mother’s son.” Taking the gun and ammo, Luke said, “I appreciate the thought. I’m not leaving you unarmed when you go back am I?”  
“Not even slightly.” Jess reached in the bag and pulled out two more guns -- one was identical to the one he’d given Luke, the other was highly illegal in the US, a Beretta 93R, an Italian machine pistol. 

Luke whistled under his breath. “I not the most knowledgeable when it come to guns but I know what that is. That takes balls.”

Jess grinned. “It’s also very hard to come by here in the US. People frown on machine guns, especially military grade ones in the form of handguns.” 

Rory massaged her temples.

Noticing Rory’s discomfort, Jess put his guns back in his bag. 

Lips pressed together, she crossed her arms and sat back in her chair. Guns, while a part of Jess’ life, were not something she was comfortable being around, especially when Luke began to get excited over them.

Jess zipped up the bag and pulled Rory into a hug. 

Rory tucked her arms in between them, letting his presence wrap around her. “I’m sorry,” she said quietly.

“Nothing to be sorry for.” He kissed the top of her head. 

Luke cleared his throat. “Rory, why don’t you check in with Lorelai and I’ll make some food.”

Rory nodded and took out her phone. Jess went to go put his bag back in his car.  
\----  
Meanwhile, Babette had just come over to see Lorelai. “Lorelai? Sugar? You here? I have got quite the news for you.” 

“In the living room, Babette,” Lorelai responded, putting down her pen and highlighter.

“You’ll never believe it, Rory’s new boyfriend Jess? He’s Luke’s nephew. Liz ran out on the kid when he was a babe, doesn’t even know her.” 

Lorelai stared, eyes wide. “You’re kidding.”

“No, ‘fraid not. Jess went off on Luke, ‘cause Luke made a rather rude comment, so Jess said: ‘If you cared so damn much why didn’t I ever hear from either one of you?’ Then everything got quiet and Luke made everyone leave.”

Lorelai’s phone buzzed and she glanced at it to see that Rory was letting her know that she and Jess were still at Luke’s. Made sense, now that she knew Jess was Luke’s nephew. “Huh. Well this is all very lucky, then.”

“How so sugar?”

[Oh yea, Luke is making us dinner so we’ll be back after. Want anything? -R]

“Oh, well Rory met him at a show in New York, so for him to randomly have an unknown uncle here in Stars Hollow is pretty serendipitous.”

[COFFEE. Also, Red Vines. -L]

Babette nodded. “He’s quite the looker too, and have you seen the car? Gorgeous.”

[Okay :) -R]

“The car?” Lorelai said tensely.

“Oh yea, Morey’s been drooling over it. 1969 2 door midnight blue Ford Thunderbird.” 

Lorelai fought the urge to pick up her pen and snap it in half. “And does this car,” she asked tersely, “have a backseat?”

“Of course sugar, most Thunderbirds do.” 

Lorelai pressed her lips together and screamed internally. “She is so dead.”

Babette looked a bit sad. “Lorelai, sweetie, you know she’s a good kid. She ain’t...she’ll be safe. Jess seems like a good kid too.” 

“No no no. Haha. See, Jess is the guy dating my daughter. Jess is the teenage rebel with a hot rod and my daughter has been riding around in it. Rory is sixteen. The same age I was when my life fell apart and I will not let the same happen to her.”

Babette shook her head. “You don’t give her enough credit, she’d never disappoint you like that. Take a few breaths, hear them out.” With that Babette left. 

Lorelai dropped back onto the couch, rubbing her left temple. “Oh God. Why?”  
\----  
Ten or so minutes later a smiling Rory and Jess arrived, with coffee, red vines and food from Luke’s. 

“We’re baaack!” Rory called out in a sing-song voice. “And we come bearing gifts!”

“Uncle Luke made a ton of extra food.” Jess followed up with. 

Rory nodded and offered her mom the coffee.

“Well, children, I am impressed,” Lorelai said congenially.

Rory smiled at Lorelai while Jess unpacked everything. 

“So, tell me about yourself Jess,” Lorelai said, returning her daughter’s smile. “You must be something special to catch her eye.”

Jess managed a smile. “I’m 17, I work for Jimmy’s company, Rory and I like most of the same books and music, and I’ve gotten her into the world of Broadway. I live in the Hell’s Kitchen/Midtown area of Manhattan. I go to a regular NYC public school...uh...” Jess wasn't sure what else to say. 

Lorelai nodded and munched a fry. “Mhm. So who’s Jimmy?”

Jess tensed up a bit. “Jimmy would be my father.”

“Ah. I’m gonna guess he’s a right bastard. Considering you called me Ms. Gilmore earlier, I half expected you to call him Father. What kind of work does he do?”

“Bastard is putting it lightly. But he does what a lot of New Yorkers do, finance, he owns his own company.” 

“He does decent for himself?”

“More than decent.” 

Lorelai sat back and brushed the salt crumbs from her hands. “Well that’s good to know. So you could take care of Rory if something were to...happen?”

Rory choked on her drink. “Geeze Mom!”

Jess remained calm. “Of course I could. I’ve worked hard for what I have, and I’ll continue to do so. But you don’t need to worry about anything happening to Rory.” 

Lorelai smiled then. “Well then for now, you’re okay by me. Except for the car.” Her expression darkened. “Yeah the car makes me nervous. Back seats tend to be inspiration for bad decisions.”

Rory shook her head, cheeks rosy. “We w-won’t…” her voice stuttered off, unsure what to really say. 

“Ms. Gilmore,” Jess said earnestly.

“Lorelai. Please.”

“Lorelai, then, to be perfectly blunt, if anything were to happen, it wouldn't be in the backseat of a car. That’s a cheap move.” 

Lorelai was impressed. “Huh. Rory, I like him, he’s honest and blunt. Keep him.” 

Rory blushed and hid her face against his chest; Jess smiled fondly and hugged her. 

Lorelai smiled. “And he’s cuter than Dean, which is what I thought must be the case when you came home with his phone number on your hand.”

Rory made a strangled sound. “No! No teasing!” she whined.

Lorelai laughed. “Sorry kiddo but that’s life.”

Rory stuck her tongue out playfully. Jess laughed a bit. 

Rory gently smacked at his shoulder. “Not funny, jerk.”

Jess looked faux hurt. “It’s not nice to hit others.” 

Rory froze for a second, wondering if she’d hurt him.

Jess noticed and understood a moment later. “Crap, Rory, that one was a joke, poor taste. I’m fine, I promise, it didn’t hurt.” 

Rory nodded, but Lorelai looked confused. Lifting an eyebrow, she wordlessly inquired after the exchange.  
Before Rory could answer Jess’ phone went off. “Shit...I gotta take this...” He took out his phone and exited the back door.

Rory met Lorelai’s eyes. “It’s not really my place…” she said softly. 

Lorelai nodded. “Give me the gist though?”

“Uhm...sometimes...sometimes Jimmy takes his anger out on Jess…” She hoped Lorelai understood that to mean Jimmy beat the crap out of him. 

Lorelai’s eyes went wide and she looked towards the door, where Jess stood, phone pressed to his ear. “Ohh…” Suddenly, things made a lot more sense.

Rory sniffled a little and quickly wiped her eyes. “I worry...”

“Oh Rory,” Lorelai said, opening her eyes and motioning Rory over to her.

Rory hugged her tight. “H-he had to go to the E.R during our movie night…I’m so sorry I lied about who I was texting...” She sniffled again, emotions from that night rushing back. 

“Sweetie,” Lorelai said, rubbing her arm gently. “The best thing you can do right now is to be there for him. It sounds like he just needs a safe place and you better than almost anyone I know can provide that.”

Rory hugged Lorelai a little bit tighter. “I love you, mommy.” 

“I love you, too, kiddo.” She dropped a kiss on top of Rory’s head. “Always.”

Rory wiped her eyes and composed herself before Jess came back in, a few moments later.

“Rory?” Jess looked a bit stressed, but was trying to hide it. “I’m going to have to go soon...” 

Rory got up and crossed the room to him. “Okay. Well...let’s take a quick walk first?”

“Of course.” He handed Rory her to-go coffee cup, and grabbed her other hand. 

Rory glanced at Lorelai. “I’ll be back in a bit. Promise.”

Lorelai ushered them out good naturedly. “Go, enjoy being young and in love.”

Jess smiled a bit. “Lorelai...nice meeting you.” 

“And you, Jess. Don’t be a stranger.”

Before they could get mushy or embarrassing, Rory dragged Jess out the front door and started towards the street.

Jess followed along beside her. “Where are we going?” 

“There’s this bridge, no one ever goes out there, where we can talk without being overheard.”

"Okay." He imagined they'd end up spending a lot of time there in the future. 

Rory smiled and led the way. At the bridge, she dropped down to the planks, dangling her feet over the edge before patting the space next to her. “Sit.”

Jess took a seat beside her and looked out over the little lake. 

“So what was the phone call about?” Rory asked quietly.

"Jimmy has another job for me. He uh... was impressed by my show of authority last week at The All Saints Tavern." 

“The job you were working before I showed up that night?”

"Yea." Jess looked over to her. 

Rory looked back at him, her eyes squinted slightly against the sun. “Just be careful okay? Come back to me in one piece.”

"I will." Jess leaned over to kiss her. 

Rory returned the kiss and smiled sadly. “I wish today had been easier on you.”

Jess smiled but it was forced. "Yea...today could have gone better." 

“Well, at least you have Luke. And, just to clarify, he’s supposed to protect me when you’re not around?”

"Yea. So let him? I can handle myself, and you, while deadly with that withering glare you have, you still need someone to keep you safe. And never leave home without the locket." 

Rory sighed. “I’ll try but it’s gonna be hard to explain this to Mom. The locket won’t come off ever except when I’m in the shower. I love it.” She dropped a kiss on his cheek. “And thanks for acknowledging my glare.”

"You'll figure it out, just eat there more often? Up the coffee intake?" Jess teased a bit. "But seriously, I'm glad you like it. "

Rory grinned and thought for a second. “What if I got a job at Luke’s? Like in the diner?”

"That's a really good idea, I should have thought of that." 

She nudged him with her shoulder. “Well that’s why you have me. I’m full of good ideas.”

"I have you for many reasons." Jess grinned.

Rory laughed. “Oh is that so?”

"Mhmhm." Jess slid an arm around her waist. 

Leaning into his side, Rory sighed happily. “So…” Her voice trailed off. “You’ll let me know when you get back to the city? And when will we next be able to talk? You told me and Luke not to call or text until you tell us to.”

"I will. I'll call you as soon as I'm home. As for the rest, I'm expecting it to be a few days." 

Rory nodded, looking sad. “Check in with me every so often?” she asked hopefully. “I mean, not that you have to but…”

"I'll call you from a burner phone." 

Rory nodded and buried her face in his shoulder. “I love you.”

Jess hugged her close. "I love you too." 

They sat there for a few minutes, making the most of the last time they had before Jess had to leave again. “I want more moments like this.”

"You'll get more, promise." Jess kissed the top of her head. He then stood up and offered her his hand. 

“I’m holding you to that,” she responded cheekily as she got to her feet. Adjusting her grip on his hand, she asked, “To the car?”

Jess nodded and led the way. 

They walked, mostly undisturbed, to the center of town where he had left his car. As they were stopping next to it, ready to say goodbye, they were interrupted by a shout. “Hey!”

Jess turned around and saw who he assumed was Dean, coming towards them. Jess slid his arm around Rory's waist. "What?" Jess said coldly. 

“Back off my girl!” Dean said angrily.

"Last time I checked, she broke up with you. Rory’s my girlfriend now, so fuck off." 

“She broke up with me because you stole her from me,” Dean accused. “So you fuck off!”

"Let's get something straight bag-boy, Rory chose me. I can actually keep a girl satisfied. So I suggest you listen close. We Mariano’s don't take kindly to threats or dickbags trying to put a claim on our women." Jess gently pulled the locket out from under Rory’s jacket and let it rest on the outside. 

Dean’s face blanched a bit. “M-Mariano?” 

Jess gave a deadly grin. "Jess Mariano, son of Jimmy Mariano." Jess walked forward and clamped a hand down on Dean’s shoulder. "Here's how this is gonna go. You're going to keep your mouth shut, since you clearly know of my Family. You're also going to stay the hell away from Rory and Lorelai. Hell, stay away from Uncle Luke too. Got it?" 

“Y-yeah, man,” Dean said, clearly terrified. “Rory, I-I’m sorry. I’ll keep my distance.”

"Good. Now run along." Jess let go of his shoulder. 

With a shaky nod, Dean turned and hurried away, figurative tail between his legs.

Jess walked back over to Rory, silently taking in her reaction. 

Rory had her arms wrapped around herself, and she looked uncomfortable but by the way she looked Jess square in the face, it was obvious it wasn’t brought on by his display of authority. “Thank you for not smashing his face in.”

Jess wrapped his arms around her. “As much as I wanted to, I knew you wouldn’t want that.” 

She smiled gently. “He’s a punk and a jerk but he’s not worth reinjurin that hand I just patched up,’ she said, adding a slight glare.

Jess kissed her cheek. “You’re right.” 

“Damn right I am,” she said, leaning her cheek into the kiss just a bit. “You are such a bad influence.” There was laughter evident in her tone.

Jess grinned. “I try.” 

Rory wrinkled her nose playfully. “Well stop.” 

“Nope, sorry, can’t.” Jess smiled playfully.

She stuck her tongue out at him playfully, before pulling away from him. “You’d better go,” she said, her tone neutral. “Otherwise you’ll never leave.”

Jess sighed. “One more kiss?” 

Rory faked consideration. “Okay. One more for the road.”

Jess kissed her with everything he had. 

Rory, slightly, surprised, sank into it, her worry momentarily fading in the way the world did when Jess kissed her.

Reluctantly, several moments later Jess broke the kiss. “Love you.” 

“Love you too,” Rory said, taking his face in her hands. “Be careful and come back to me in one piece.”

“I will.” Jess kissed her once more before he broke away and unlocked the driver side door. 

Rory stood on the sidewalk and watched him climb in and start the car. Her arms had returned to her middle and it looked suspiciously like she was trying not to fall apart in the middle of town with everyone watching her. Jess pulled away from the curb and drove down the street, turning and then he was out of sight. He turned his music up as loud as he could stand it, trying to block out his thoughts of Rory and worry about what was to come back in New York.


	8. War

The day after Jess’ somewhat disastrous visit to Stars Hollow, Rory dragged herself to school with what felt like a ten pound weight on her chest. He’d called her when he got home, but he’d only stayed on the line for a few minutes before imposing the communications ban. She made her way to the library during her free period and took out the book Jess had picked out for her the day they’d hung out in Hartford. Rory plopped down in a cozy nook near the back of the library and settled down to read, absentmindedly playing with her locket as she read. 

Paris and Tristan, looking to get to work on a project for history, made their way towards the tables in the center of the library, but before they could get started, Paris realized she needed a book and went off to grab it. As she looked, she noticed Rory tucked into the comfiest nook in the library. “What is she doing here?” she muttered.

“It would appear that she’s reading,” Tristan said point blank. 

Paris rolled her eyes and flung her hand in his direction like she was going to gently smack him with the back of her hand. “Obviously, but what? And why is she here if she’s not working on a project? It’s a very nice day outside. Plenty of space in the courtyard.” That was when Paris noticed the locket. “What is that?”

Tristan pulled Paris behind the bookcases so they could get a better look without being noticed. “Looks like some antique locket, has a coat of arms on it. Think it says Mariano at the bottom...” 

Paris peeked around the bookcase and narrowed her eyes. “I’d bet that’s a mob locket.”

“Mob locket?” Tristan raised an eyebrow. 

“It’s a locket, usually passed down parent to child, for the heir to give to the person they love, a way of claiming them before there’s any sort of formal engagement or anything. It’s the best form of protection a girl can have in a mob city.”

Tristan made a choking noise. “Holy shit…” he took a moment to calm down before speaking again. “How do you know all this?”

“My dad has...connections. He’s not actually mob but he makes a lot of business deals with mob run companies.”

Tristan blinked. “Wow… so what do you know about Mariano’s old man? Have you ever seen him?” 

“No. He almost never deals with people like my dad. Has his right hand man do that. Jimmy Mariano is a total bastard,” Paris said, somewhat darkly. 

Before they could chat or speculate anymore, the warning bell rang. Rory gathered her things and headed towards the exit. 

“We’d better go,” Paris said quietly. “I want to keep an eye on her.”

Tristan nodded and followed Paris out of the library. 

Rory was oblivious to their continued observation as the day progressed and when it was over, she moved to the bus stop in a daze, her face clearly worried. In her nervous state, she fidgeted with the locket as she waited, her hands needing something to do. The bus to Stars Hollow pulled up about two minutes later; it was relatively empty. 

Rory climbed on and Paris stared, willing her to look her way. “Something’s going on. She’s flipping out about something, and from the way she’s fiddling with that locket it has to do with Mariano.”

“Maybe she’s worried about him? He could be on a job? Maybe see if you can snoop around for info from your dad. Like, if Mariano got a promotion or something?” 

Paris considered. “Wouldn’t hurt. And I could always pass it off as taking an interest in the family business,” she said thoughtfully.

“Cool, keep me posted.” Tristan scribbled his number on Paris’ hand and then walked off.

Paris blinked at the number and fought the urge to squeal. Tristan’s number was on her hand. Her hand for Christ’ sake! “O-okay.”

Not a moment later the bus pulled out, making it’s way back to Stars Hollow. The trip passed in a daze as Rory continually checked her phone, hoping against any sort of logic and hope she could think of that an unrecognized or blocked number would flash across the screen, reconnecting her to Jess if even for a brief moment.

[Things are in motion. 2 Days.] 

Her heart stuttered. Jess. [Okay. I love you. -R]

[Love you too.] 

No more texts arrived after that. Rory sadly exited the bus and headed to Luke’s. She took out her phone to text Lorelai. [Meet at Luke’s? :) -R]

It took a minute, but Lorelai finally answered. [I’ll be there in twenty. :) -L]

[Okay :) -R]

Rory walked into Luke’s and took a seat at the counter. “Hi Luke!” 

“Hey, Rory. How was your day?” The diner was mostly empty, and before Rory could respond, the one or two people inside dropped a few bills each on the tables and made their way out.

“It was pretty good, I was thinking though…” Rory fiddled with the locket. “What if you gave me a job here?” 

“You mean like after school?” Luke asked as he wiped down the counter.

Rory nodded. “And like, days when I don’t have school and Jess isn’t visiting.” 

That caught Luke’s attention and it was obvious the second her idea clicked in his head. “Ahhh. I imagine we can figure something out.”

“Yay! Thanks Luke!” Rory jumped up and hugged him. 

Luke laughed and was startled for a second before hugging her back. “Not a problem.”

Rory and he talked about hours and responsibilities and pay, settling everything before Lorelai arrived.   
“Well hey there, stranger,” Lorelai said as she made her way inside and sat down next to Rory at the counter. “What are you two conspiring over?”

“Luke gave me a job!” Rory said brightly. 

“Oh really?” Lorelai said, her interest tinged with slight indignance as she gave Luke a very pointed look. “Mind if I talk to you alone Luke? Just for a second.”

Rory gave her mom a pleading look. Luke simply nodded and gestured to the store room. Lorelai made her way back there and readied her glare.

“Yes, Lorelai?” Luke crossed his arms. 

“Just what the hell do you think you’re doing, giving her a job? She has so much on her plate already and I really don’t think she needs the stress of regular hours somewhere!”

“Lorelai, calm down. Rory asked me for a job. She said it would be perfect for her college application and she could make some extra money. We worked out the hours, nothing too much, so she’ll have plenty of time to study and whatever.” 

Lorelai let out a heavy breath through her nose and her glare softened just a bit at the mention of college applications. “Okay,” she conceded. “But the moment I think she seems overloaded and overworked, I’m pulling the plug. No ifs, ands, buts or ors. I’ll give two weeks notice and then she is done. Got it?”

Luke nodded. “That sounds fine. But I wouldn’t worry, she can use down time to work on stuff, I’ll put a table in the storeroom or something.” 

“Fine.” Lorelai turned and walked back out to the counter to sit next to Rory. Luke smiled and shook his head before heading back to the kitchen. 

“I assume I can ask for coffee now right? Or is there more shocking news I should hear first?”

Rory nodded. “No more news.” Luke came over with two coffees not a second later. 

Lorelai gratefully accepted hers and took a gulp. “Good because I don’t think I could take it.”

Rory giggled into her cup. “How was your day?” 

“It’s been busy and doesn’t show any sin of stopping,” Lorelai said truthfully.

“But that’s good!” 

Lorelai shrugged. “I guess so. But tomorrow is busy, what with that wedding…”

Rory nodded sympathetically. “You should head home and take a nap. I’ll bring food by later.” 

“Are you starting today?” Lorelai asked, surprised.

“Well...I was going to? I did all my homework during lunch and free period.” 

Lorelai looked her in the eye to judge how stressed Rory looked and sighed. “Fine. But let me know when you finish so I know when to expect you home okay?”

“Of course!” Rory hugged her. 

Lorelai returned the hug and smiled gently. “I’ll see you later.” 

After Lorelai headed out Rory got to work, grabbing an apron and putting a pad and pencil in the front pocket.   
“Tomorrow, make sure you’ve got a change of clothes alright?” Luke said. “Last thing I want is to have your mother yelling at me for your uniform getting a grease stain.”

Rory nodded. “Noted.” 

Luke went back to cleaning up the counter. “So...you seem to be taking the whole, “My-boyfriend-is-a-mobster-set-to-inherit-a-criminal-empire” thing rather well,” he commented.

Rory shrugged. “I had my suspicions before he confirmed it and went on a research binge. Still on one to be honest. What all do you know exactly?” 

“Well, I know that Jimmy is currently in the Seat and Jess just got promoted to Right Hand, officially putting him in line as the Heir. I know he’s dealt with some serious crap to earn that. and I know he’s got some nasty scars from things he’s gone through. And that he has connections. All I need to know.”

Rory paused debating on telling Luke, but finally gave in. She couldn’t keep it bottled up. “Jimmy beat the crap out of Jess and I heard everything over the phone cause he accidently dialed me...and it...it was really bad..Jess had to go to the ER.” The words just flooded out. 

Luke was stunned into silence. “Is that why he had rib tape on yesterday? Why he had such nasty looking green bruises?”

Rory nodded. She took out her phone and pulled up the pics Jess had sent her while at the ER. 

Looking at the pictures, Luke scowled. “If I didn’t know Jess already had something planned, I’d be headed over to kill that bastard,” he hissed.

Rory’s eyes widened. Instinctively she figured Jess was doing something along the lines, but there had been no confirmation. “H-he’s really gonna kill him?” 

Luke shook his head. “I’m not one-hundred percent on that, but I do know Jess has some plans that I definitely don’t want to be in the way of. And that we definitely need to keep you away from.”

Rory sighed and drained the rest of the coffee from her cup. “Yea...he did message me though. Said: Things are in motion, 2 days.” 

Luke nodded and went back to cleaning. “Sounds about right.”

They had to cease the conversations when the dinner rush started up. For a few hours, both Rory and Luke were almost constantly on the move, taking orders and delivering them to tables as fast as possible. Before Rory even knew what hit her, Luke was preparing to close up for the night. “Go home, kid. And text me when you get there so I know you’re okay. I’d walk you home but I got some stuff to take care of.”

Rory nodded and smiled. “Night Luke.” Rory headed home with her and Lorelai’s dinner. It was misty but not so bad that she couldn’t see, and when she stopped in front of the house to see lights on, she grinned. Rory headed on inside. “Mommmmmmm! Food!” 

“And so the prodigal daughter returns, bearing the spoils of her toils!”

Rory laughed and unpacked their food on the kitchen table. She paused to text Luke. [Home now. -R] 

[Good. I may drive by later just to make sure everything’s okay. Good night. -L]

[Okay, night. -R] 

“So what did you bring us?” Lorelai asked gleefully.

“Burgers, two sides of fries, onion rings to share, and coffee of course!” 

Lorelai sighed happily and grabbed a burger. “Maybe you having this job isn’t so bad after all.”

Rory laughed. “Knew you’d warm up to it sooner or later. Plus, it gives you even more of a chance to flirt with Luke.” 

Lorelai gasped and nearly dropped her burger to the floor. “I do not flirt with Luke!”

“You do! You so do!” 

Lorelai squinched her eyes closed. “Rory, I do not flirt, I banter. I tease. But flirting? No. Not at all and I am appalled that you would even suggest I ruin my and Luke’s friendship with that!”

“But you guys would be so perfect together! Everyone know you guys have a thing for each other.” 

“We do not have a thing okay?!” Lorelai knew she was protesting just a little too hard but the denial was strong.

Rory grinned. “Someone doth protest too much methinks.” 

“Dammit child!” Lorelai muttered. “Look,” she said with a heavy sigh. “Even if we had a thing for each other, it wouldn’t go anywhere, nor would it end well.”

“I think you’re wrong. But I’ll leave it, for now.” 

“I appreciate it but I would appreciate it even more if you totally forgot it.”

“Nope.” 

“I had to try.” Lorelai bit into her burger. “Well at least he cooks well…” she grumbled.

Rory took a handful of fries, trying not to giggle anymore. 

“I see you trying not to giggle. I’m glad you’re having a laugh at my expense.”

“I love you Mommy,” Rory tried to say innocently but dissolved into more giggles.

Lorelai rolled her eyes and got up, taking her food with her. “I’m going to work on some stuff. Come find me when you’re done dying.”

“Aw N-No! Come back!” Rory tried to catch her breath. 

“Uh uh. Not happening. At all.”

“Mooooooooooooom!”

“Rooooooooooooory!” Lorelai imitated. “I’ll be in the living room.”

“Fine, mean!” Rory got comfy again and resumed eating. 

“Yeah whatever drama queen.”

Before Rory could reply, the phone rang. “I’ll get it!” Rory grabbed the phone off the receiver. “Hello?” 

“Rory? It’s your grandmother.”

“Oh hi Grandma,” Rory said sweetly.

“Sorry to be calling so late, but we need to move our Friday Night Dinner to Thursday this week, your grandfather has a flight to Boston Friday afternoon.” 

“Oh really? Lemme check with Mom real fast.” Rory gently set the phone down and scurried in to Lorelai. “Mom? Grandma has to change dinner to Thursday because Grandpa has a flight to Boston Friday Afternoon.” 

Lorelai looked up from her textbook. “Really?” she whined. She tilted her head questioningly. “Why? Dad not being home has never stopped us having dinner on Friday before.”

Rory shook her head and went back to the phone. “That’s fine Grandma, we’ll be there.” 

“Oh wonderful!” Emily enthused. “Your grandfather will be so pleased. And I’ll have the staff make those wonderful apple tarts you and your mother love so much, yes?”

“That sounds great.” Rory smiled. 

“Well I look forward to seeing you Thursday.”

“Bye Grandma! See you Thursday!” Rory hung up the phone and returned to her food. Then she realized...Jess had told her two days. That meant Thursday….  
\--------  
Jess Mariano suited up and made sure his shoulder holsters were sitting in place, he had a bullet proof vest under his suit coat as well. Grimly, he fixed his tie and checked its position in the mirror. he certainly hated his father but killing him was not something he wanted to do. It would be a mess not worth cleaning up. Sighing he did a double check of his weapons and ammo stashes, he’d made sure to have a few knives stuffed away as well, just in case of course. Finally, he could delay no more and he made his way to the elevator, praying that Rory was safe somewhere near Luke. He’s timed this as well as he could to make sure she would be hidden away in Stars Hollow and not Hartford or New York. Jess stepped into the elevator and selected the garage floor. The door dinged open a matter of moments later. He breezed over to his car and got in, wasting no time. First up, Velasquez, Defranco, Novelli and Alberti. They were among his father’s most loyal. 

It was a 10 minute drive ‘til Jess reached the Velasquez residence. He made his way to the door and knocked once. A housekeeper, short and plump, answered the door. “May I help you?”

“Mr. Mariano, here to see Mr. Velasquez.” 

The woman stepped aside. “Business or social?”

“Both.” Jess smiled charmingly. 

The woman blushed a bit and closed the door behind him. “I’ll let him know you’re here. You can wait in the living room through that door,” she said indicating an arch covered in beautiful wrought iron curlicues.

“Actually, if you don’t mind, I’d prefer it to be a surprise.” Jess handed the women a $50 and walked silently down the hall and to the study. He took out his gun and swung the door open. Before Velasquez could even speak, Jess had put a bullet in his skull. The ping of the silencer echoed in the quiet house. The rest of the Velasquez family, thanks to Jess, had been sent on a vacation to The Hamptons for the weekend.

Jess exited the house just as quickly as he’d entered and set off towards the Defranco residence. They had a place in Chelsea. Jess wondered if the bribe he’d delivered to the Chief of Police to silence any possibility of charges against him was enough. If not, there was more money. Perhaps even a donation of some fancy tech for the training academy, something to draw the recruits in. 

Jess parked a block away from the Defranco’s building and walked the rest of the way. He’d managed to make it to their floor undetected. The Defrancos were a bit more high profile than the Velasquezes. Jess knocked once on the door. 

A young woman opened the door, clearly tired, but still clearly ready to deal with just about anything. “Can I help you?”

“Missy, who’s at the door?” Defranco called out.

Jess covered her mouth before she could speak and grabbed his gun. He quietly shut the door behind him. “You will not scream and you will say exactly what I tell you. Mr. Mariano is here to see him, with good news.”

She nodded, eyes wide. When he uncovered her mouth she whispered, “Can I leave before you? Last thing I need is his wife comin’ after me.” 

“You may leave with me. I’ll make sure you’re safe Missy. Now, tell him what I told you too.” 

She nodded. “Mr. Mariano’s here to see you. Says he has good news.” Her Long Island accent made it sound like she had gum despite the fact she was obviously preparing for bed.

“Ah, Jimmy--” Before he could say another word, Jess was across the room and had him pinned up against the wall, gun to his temple. 

“We’re going to go have a chat.” Jess marched him into the hallway between the Kitchen and bedrooms and into the office. Jess kicked the door closed behind them. 

“Come on, kid. You ain’t got the guts to take over your dad’s spot.” Defranco was clearly trying to put up a front. Jess could feel him shaking. “It takes more gall than ya got in all of ya to fill his fuckin’ little finger.”

“I’m going to have to disagree, considering your buddy Velasquez’s brains are painted across the back wall of his office.” 

For a second, Defranco froze and then he began to struggle violently, doing his best to throw Jess off of him. “You little fucker!”

Jess shot a round into Defranco’s left kneecap, taking him down to the floor in an instant. 

“Argh!” the man gasped, doing his best to keep quiet, as he’d been taught to.

“Here’s how this is gonna go. I’m going to blow your fuckin’ brains out, then I’ll do the same to Novelli, and Alberti, then I’m gonna pay my old man a visit.” 

“You little shit. The whole empire will collapse under your incompetence,” Defranco said, spitting in Jess’ direction. His voice wavered and he was rocking back and forth, clearly in pain.

“That’s where you’re wrong. I’ve got the entire family’s support. I’ve been running this city while Jimmy and you all sit on your asses. I have the NYPD eating out of my hand. And those of you who oppose? Well, you get this.” Jess raised his gun and fired the kill shot into Defranco’s head.

Missy knocked tentatively at the door. “Jess? Is he...y’know…?”

Jess exited the room in a way that Missy wouldn’t see anything. “Yes, so I suggest we leave now.” 

She nodded and hitched her bag up on her shoulder, her thin spring dress hanging haphazardly on her thin frame. “Lead the way.”

Jess walked her to the curb and gave her money for the taxi. “Be careful.” With that, Jess headed back to his car. 

“Jess?” she called after him. “You’re gonna protect me from Francesca right?”

“Of course. Head home, straight home. I have a man or two to spare you until she calms down.”

Missy nodded and turned to hail a cab. When one stopped, before climbing in, she called out, “You’re a good man, Jess Mariano.” With that, she ducked into the car and was gone.

Jess took care of both Novelli and Alberti in under an hour before he headed to his father’s office building. It was then that he made sure the Beretta 93R was ready to go, due to the high security he’d meet. With a glance around the street to make sure no one was around, Jess made his way into the building, preparing to face off with any number of his father’s goons. He didn’t bother stopping at the front desk and bypassed it for the elevators. 

“Hey! Kid! What’re you doin?”

Jess hit the elevator close button just in time and the elevator headed for the top floor; Jess immediately shot out the elevator camera and moved to the side away from the doors. 

There would be more goons waiting between him and his father, but the chances of them being any real challenge were slim. Growing up in seedy, rough neighborhoods had made him an excellent shot.   
Jess stepped off the elevator and began his walk down the hallway. He shot out each hallway camera as he came to them. 

“Kid, you’d best clear out,” a voice growled at him. One of his father’s meatier goons stepped out from the shadows. “Your pops ain’t too happy right now.”

“First of all, it’s Jess Mariano, Mr. Mariano to you.” Jess shot out both of his kneecaps in rapid succession with the Beretta. “Second of all, I don’t give a damn what makes my ole’ man happy.” 

The goon seemed to shrink in on himself, and his eyes widened in respect. “Noted, Mr. Mariano. Have a nice evening.” Jess smiled as he disarmed the goon. 

“Maybe I’ll let you live after all.” He walked away without a backwards glance. 

The next few goons, having overheard the exchange, looked down and stepped back, guns on the floor in front of them as they murmured, “Evening Mr. Mariano, sir.” And then...Bruce, Jimmy’s favorite bodyguard stepped out of the darkened doorway to Jimmy’s office.

“Back off, kid,” Bruce said in his hoarse rasp of a voice. “The Boss said no interruptions. He’s trying to figure out who offed his advising board.”

“That’d be me.” Jess raised the gun and fired two rounds into Bruce; one had been more than enough to kill him, but he really did not like Bruce. Before entering the office, Jess turned towards the disarmed guards. “Get out of here! NOW!” 

The men scrambled to the elevators, making sure not to look Jess in the eye for fear of seeming disrespectful. They knew their places and they knew Jess was about to take the one he wanted by force.

The door swung open and Jimmy, face as mean as ever, leveled a glare at him. “What do you want, screw up? Come to tell me you failed yet again?” That was before he noticed Bruce. “What the hell?!”

Jess raised the Beretta up. “I’d raise my hands if I was you.” 

“You little jackass!!” Jimmy said angrily. “I knew I should have killed you when I had the chance, heir or no. You’ve been nothing but a--”

Jess fired a warning shot into the doorway less than a millimeter away from Jimmy’s head. 

Jimmy jumped and looked back over his shoulder to where the bullet lodged in his chair, then back at Jess, eyes wide with sheer panic. He gulped and raised his hands shakily. “Come on kid, l-l-let’s talk about this. I been good to ya, took care of ya after your mom ran off and your uncle disappeared --”

Jess backed him into the office, gun raised. He made sure to shut the door behind them. “See, that’s not what Uncle Luke told me. And frankly, you’ve been a pretty shit father.”

“Oh now come on,” Jimmy said, slightly desperate. His eyes flew about the room, obviously trying to gauge his chances of reaching one of the stashed guns. “I made sure you had food and clothes and-- AHHH!” Jimmy cowered away from the gun pressed to his temple.

“Sit, hands on the desk.” Jess’ tone was colder than ice. 

Jimmy, still desperately looking for a way out, did as he was told, the cold of the wood seeping into his skin and making him shudder.

Jess had two stilettos out before Jimmy could even process what was going on. Jess slammed the first down, lodging it through Jimmy’s right hand and into the desk. Jimmy screamed bloody murder and try as he might, tears began rolling down his face, splashing onto the desk to mix with the blood pooling there. Jess did the same with the second stiletto only a few seconds after. 

Jimmy’s breathing was labored and he was sniffling as his nose began to run.

“Oh don’t be such a baby. I’ve had worse than this. Hell a lot of it was your doing. You aren’t a father, Jimmy, you’re an abusive shithead who had no business with a kid. You also lied to me, you lied to Liz and you lied to Luke. I had chance after chance at knowing them, and you blocked every single one of them.” Jess’ voice was disconcertingly calm. 

“But...but…” Jimmy gasped. “I was doing...what I thought...was best.”

“BY KEEPING MY FAMILY AWAY?! I DON’T KNOW MY OWN MOTHER!” 

Jimmy grinned. He’d gotten what he wanted. “No, and unless you let me go, you never will.”

It was Jess’ turn to grin. “Nice try. I have Liz taken care of. You and I though, we’re gonna chat.” Jess sat on the edge of the desk, away from the blood flow. “Velazquez didn’t even have time to blink before I had his brains painted on the back wall of his office.” 

Jimmy blanched. “You couldn’t do that to me,” he bluffed. “I’m your old man. No matter how much you hate me, you’ll never--”

“Now, Defranco, I toyed a bit with first. He did disrespect me after all. He was quite loyal to you. The others... I had them offed in less than an hour. Really, it was all too easy.” 

Jimmy instinctively went to slap Jess, letting out a cry of pain when that caused the knife to rip his hand up further. “Bastardo, figlio di puttana!! Ahhh vaffunculo, stronzetto!” 

Jess smirked. "See you in Hell." Jess pulled the trigger and shot Jimmy in the chest. He wanted to watch him bleed out. Jimmy didn't deserve a quick death. 

Jimmy wheezed and a few specks of blood flew out of his mouth. “You know kid, we aren’t that different, you and me. And I’m proud of how much you remind me of me -- desperate, greedy, and power hungry. That little puttana you’re seeing? She has no idea what’s coming. She won’t stay.” He wheezed again. “Like your mom, like mine.” 

Jess forced his emotions down before he clamped a hand on the back of Jimmy's neck and forced Jimmy to look him in the eyes. "She knows everything. And she loves me. She also hates you to the core, mentioned poisoning you. Don't underestimate my girl. Everyone underestimated me and now look where I am."

Jimmy tried to spit in Jess’ face and failed miserably. “You’re going to fail at running this family.” His voice was raspy and breathy all at once.

Jess grabbed one of the stilettos and pulled it from Jimmy’s left hand; he slit his throat in one graceful movement. 

There was a final gurgle from Jimmy’s gaping throat and then he went silent, his eyes dulling, muscles relaxing in the absence of motor impulses. Jess pulled the last knife from Jimmy and dumped his body on the floor to the side of the desk. He wiped The Seat off and sat down. A moment later he turned on the building wide intercom and spoke with a tone of icy authority. "This is Jess Mariano, Mr. Mariano to all of you. I suggest someone gets up here and cleans my office immediately. The rest of you I expect to assemble in board room A." With that he signed off.

Almost immediately, the sounds of those still around working late scrambling towards the board room filled the building with almost enough noise to make it sound like a regular Monday morning. A cleaning crew, two youngish looking guys, moved in with the whole array of products and containers, prepared to handle anything the new Boss might throw their way. They murmured “Good evening, Mr. Mariano,” before going about their work and kept their heads down.

Jess waited till they’d left before he called Luke. 

“Hello?” Luke answered warily.

“It’s Jess.” 

There was a clearly audible sigh of relief and then Luke said, “Thank God you’re okay.”

“Where’s Rory?” 

“She’s in Hartford. Her grandmother insisted on moving their weekly dinner to tonight because Rory’s grandfather leaves for Boston tomorrow.”

Jess let himself relax, but soon tensed again. “I was going to let him bleed out, shot him in the chest, but then… then he called Rory a slut, so I slit his throat.” 

Luke whistled under his breath. “Woah. How did he even know about her?”

“Probably had someone follow us, I’ll handle it. I’m doing an entire security reconfiguration as well as revamping the entire family. I just wanted to let you know I’m okay. I’ll call Rory later, but I won’t be back in Stars Hollow until Sunday at earliest.” 

Luke grunted. “Figured. She’s worried sick about you though so maybe she can come visit?” he suggested. “Also am I right to assume Jimmy calling her a whore doesn’t leave this phone call?”

“No, absolutely not. I don’t want her anywhere near New York, I don’t want her anywhere alone either. Look, I’ll call her in a little bit. And definitely don’t tell her what Jimmy called her. I’ve got to go now.” Jess hung up and headed to board room A.

The room was bustling despite the somewhat odd hour and people immediately silenced when they saw Jess in the doorway. They’d made sure to get all those who weren’t present, up on skype. Jess took a seat at the head of the table. “There’s going to be quite a lot of changes around here.” 

The silence intensified, with no one even shifting in their seats or clearing their throat.

“Now.” Jess slammed his fist down on the table. “Which of you fed Jimmy info about Rory Gilmore?”   
No one moved.

“I’ll be inclined to go a lot easier on you, if you speak up now versus, later.” Jess opened his suit jacket to reveal the Beretta, indicating that’s what would happen later. 

A tentative hand went up. “It wasn’t me directly, but it’s my department,” Roscoe said quietly. “I’m sorry, sir.”

Jess took out the Beretta and shot him in the shoulder -- it wouldn’t kill him by any means, but it’d get the point across. “No one, No. One. Is to lay a fucking finger on Rory Gilmore, don’t even look at her. She wears my locket. DO I MAKE MYSELF CLEAR?!” 

There was a general consensus of “Yes, very” and everyone went silent again.

The next hour was spent making a few much needed security adjustments, outlining how things were going to go from that point on, and putting his most loyal in the proper positions of power. At the end, a few bodies had to be removed as well, and others were to be seen by medical teams.

Jess rubbed his temples and sighed. “Alright those of you not in need of a stretcher or body bag, OUT!” The group scrambled to remove themselves from his presence before more injuries could be given. Jess gave out orders to those who remained, and the medical teams before he retreated to his office. He knew that was the one place completely free of bugs and cameras, and it was virtually soundproof. Jess settled into his seat and took out his phone. [Can I call? -J]

Rory, doing her best to appear untroubled, jumped a little as her phone buzzed. She checked it under the table and replied [Give me ten minutes for extraction. -R]

Before Rory could ask to be excused, Emily spoke up. “So Rory, I hear there’s a rumor going around that you have a new boyfriend. Is it true?”

Rory smiled. “Yea, uh, I do. Jess, Jess Mariano.” 

For a split second, Rory could see Emily’s smile waver. She shared a look with Richard but it was quickly masked with smiles. “Oh really?”

“Yea, they met in New York when Rory saw Phantom of The Opera with Chilton. They had seats next to each other. Nice kid,” Lorelai chimed in. 

Emily forced a smile. “I’m sure he’s quite lovely. Perhaps you’ll bring him to meet us sometime?”

Rory hesitated. “M-maybe. May I be excused? I need to use the restroom.”

“Of course dear,” Emily said with a smile.

Rory hurried off to the restroom and called Jess as soon as she was shut inside.

“Hello?”

“Jess?” Rory asked worriedly.

“Rory.” Jess relaxed. “I just wanted to call you to say that everything has been handled, and I’m okay.” 

“Oh thank God,” Rory exclaimed. “I’ve been a nervous wreck all night, I’m sure my grandparents have noticed.”

“I’m sorry for worrying you...I love you. I won’t be back to Stars Hollow till Sunday at earliest though, I need to pay the big clients and allies a visit.” 

Rory sighed. “Okay. Can I come to New York, or should I just...stay put?” She fiddled with the locket.

“Stay put, I don’t want you anywhere near New York, till I’m sure I’ve fixed the security problem.” 

She squinched her eyes shut. “Okay. I love you, Jess. And I miss you. Is it at least okay for me to text or call you?”

“Text yes, calling I’ll have to do since I’ll be in and out of meetings. Rory...I love you too and I miss you terribly. Let me know when you get home.” 

“I will,” Rory said, her voice pinched. Whether her tears were from pain or relief she couldn’t tell. “Thank you for telling me you’re okay.”

“Always, Rory. You’re the most important person in my life. I’ve got to go now though...I’ll try to call tomorrow.” 

“Okay. I love you.” She felt like she always said that but she meant it and felt like he needed to hear it.

Jess smiled a bit. “Love you too, bye Rory,” he said, hanging up not a second later. He could really use a drink and a shower. 

Rory slid her phone into her pocket and sighed, laughing just a bit as she wiped at her teary eyes. She was a mess. In a rush, she used the restroom and made sure to splash some water on her face to make it seem less like she’s been crying and more like she was just tired. Meanwhile, Lorelai and her grandparents had made their way back to the living room and were waiting to say goodnight. Rory stepped in, smiling. 

As Rory made her way in, Emily felt her eyes widen and her jaw tense. She was wearing a locket that not only said Mariano but had the family crest on it, and from the size and prominence of the piece, Emily was willing to bet it was, in fact, a mob locket.

“Such a shame you have to leave early tonight,” she said congenially.

Lorelai smiled, “Yea well, school and work waits for no man! Come on, kid.” She linked arms with Rory. 

Rory smiled and waved to her grandparents as she and Lorelai made their way out. “Bye Grandma, bye Grandpa. See you next week!”

Emily waved weakly and shut the door behind them. “Richard!” Emily tore through the house to the study, where he’d no doubt, disappeared to. 

“What is it, Emily?” he asked from behind his paper.

“Our little girl is involved with a mobster! The...the Mariano heir!” 

He lowered the paper slightly and looked at her over his glasses. “Well she did mention his name but the chances of there only being one Jess Mariano in New York City are somewhat slim.”

“She’s wearing his locket!” Emily all but shrieked. 

That got the paper put down completely. “You’re certain?”

“The name and crest and everything is on it!”

“It would appear our little girl is more like Lorelai than we thought after all.” Sensing that Emily needed comfort, Richard stood and pulled her around the desk to hold her.

Emily sniffled. “Richard, I think she knows what he does, she wouldn’t be wearing the locket if she didn’t.” 

“Well this is something we have absolutely no control over, Emily. It’s a decision, and possibly mistake; she has to make for herself.”

“Isn’t there anything we can do?” Emily asked, growing more distressed.

“Emily, she’s wearing the locket. That means he’s laying a claim to her and he’ll do anything to protect her and keep her. Unless we want to be nursing new pairs of dentures by Monday, we have to stay out of it.”

Emily sighed and wiped her eyes. “You’re right...” 

Richard hugged her closer for a second and smiled gently. “I suspect she’ll be just fine.”

Emily hoped he was right.

**Notes for the Chapter:**

> Translation of what Jimmy yells at Jess.   
> Bastardo, figlio di puttana!! Ahhh vaffunculo, stronzetto!-- Bastard, son of a whore! Ah fuck you, you little shit!


	9. I Want You: part 1

**Notes for the Chapter:**

> This is part 1 of this chapter, but since it's such a long chapter I felt it would best work split. Part 2 will be up shortly.  
> Briefly in this chapter a few Life With Derek characters will be mentioned/referenced. This fic will remain solely Gilmore Girls, but the sequel, as planned from the beginning with PrincessaKyla, will be a bit of a crossover. No worries though, the focus will remain on Jess and Rory.   
> The poem Jess sent Rory is a portion of If You Forget Me by Pablo Neruda

Jess walked into his office and shut the door. He fixed himself a drink before taking a seat at his desk and propping his feet up. It was great to be back in New York after jetsetting around the country the past few days. He was down to two more meetings before he could go see Rory. He took a moment to enjoy his drink and the silence of his office before reaching for the phone. It was time to give one his biggest allies, the Venturi family, a call. He’d decided against going to see them since it would mean crossing the border into Canada and he did his best to limit those crossings. Too many could draw attention. Jess picked up the phone and dialed the direct line. 

“Hello?” A woman, Jess was willing to guess Venturi’s wife Nora, answered. 

“Mrs. Venturi, it’s Jess Mariano, head of the Mariano Family.” 

There was a sound of slight surprise but Nora kept her composure. “Jimmy’s son, right? Is he alright?”

“Jimmy’s no longer with us. I am in The Seat now.” 

“Ahh. I see. I suspect you’ll want to speak to George then?”

“Yes thank you.” 

There was quiet murmuring in the background, and Jess could just make out, “Jimmy’s heir” before there was the scuffling of fabric and George came on the line. “Hello, Jess. Long time no chat. So Nora tells me we’ve lost your father?”

“Not so much lost as I put a bullet in him and slit his throat when he decided to mouth off.” 

George made an appreciative noise. “Good on you kid. I don’t need to tell you how much of a bastard he was.”   
George’s tone was pleasant, but it was obvious he was evaluating Jess, deciding whether or not he was pleased by the change of hands. “And, if I may. What was he mouthing off about?”

“You never call a man’s woman a whore.” 

George’s voice darkened. “No. No you don’t.” There was a moment of silence, and then George offered, “Our alliance is ensured I assume? You and Derek have always been on good terms, and you seem to be capable of running the Family and the business.”

“Of course, in fact, that was my main purpose for calling. Jimmy was an incompetent, poor excuse of a businessman among other things. Defranco had no business being Jimmy’s right hand. Thus, I’d like to offer that to you.” 

“An even stronger alliance?” George sounded thoughtful. “I was contemplating sending Derek and Nora’s daughter Casey to Toronto so Casey could go to school in New York…” he murmured. 

“It’d be easy to secure them a spot at NYU.”

George was impressed. “Really? You’ve outdone yourself. I imagine Derek will stay in Toronto but Casey will gladly accept.” There was a pause. “Consider us your new right hand family, Jess. Is there anyone you have in mind for emissary? On either side.”

“If you think he’d be up for it, I think Derek would be a good fit.” 

“Only if you don’t mind waiting until summer. He’s determined to graduate and he wouldn’t dream of leaving without Casey.”

“That’s fine. I can have Julian Zaccaro stand in for him in the mean time.” 

“And might I ask who you might be sending to us? Just so I can go about making arrangements for housing.”  
“I’ll be sending Dante Valente.” 

“Alright. Well we’ll have everything ready when he arrives,” George said firmly. “Jess, I appreciate you letting us know about your old man and the strengthening of our alliance. I take it from your earlier comment that you’ve found a young lady to take charge with you?”

“I have, Rory Gilmore.” 

“Is she, by any chance, related to Richard and Emily Gilmore of Hartford?”

“She is, Rory is their granddaughter.” 

“Ahh. A fine choice. I ask because I wanted to offer my wife Nora’s guiding hand if Rory would like it, or if she feels somewhat lost. Judging by her background, she has no experience with the life.”

“Rory and I both appreciate that. I’ll have Rory get in touch with Nora.” 

“I’ll be sure to let her know. I’ll have Derek get in touch with you as well.”

“Sounds good, pleasure doing buisness with you, Venturi.” 

“Same to you, Mariano.” 

There was a click and the call ended, leaving Jess once again in the peace and quiet of his office, though, not for long. Jess pressed on the intercom, beckoning his assistant, Annalise in.

She poked her head in the door. “Sir?”

“I want a dozen red roses sent to Rory Gilmore at this address, immediately.” Jess handed her the address to Luke’s diner, knowing she was currently working. 

“Yes sir. Anything for the card?”

Jess scribbled a note down and handed it to her. 

Annalise nodded. “Very well, sir. Anything else?”

“No, that’s all. Forward any top priority calls to my phone. I’m expecting to hear from GQ.” 

“Of course sir. It will be taken care of sir, you have my word.”

Jess smiled. “Thank you, Annalise.” Jess grabbed his bag and headed for the garage. 

It was empty sounding as he made his way through, mostly due to the sheer number of people who had been disposed of, either bodily or simply in terms of their official job with the company. Quite a few were out on assignment, and there were several people, including Roscoe, who were still out on medical leave. Jess unlocked the door to the Thunderbird and got in, immediately putting in a CD. He roared out of the garage, a grin on his face. One last client and then...then he got to see his girl.  
\----  
Paris and her father were arguing, yet again. “Dad. How am I supposed to get a feel for the business if you don’t let me sit in on your meetings?”

Alexander Geller rubbed his temples. “Paris, I have no problem having you sit in on meetings, but Jimmy Mariano is a very important client!” 

“And he’d be sooo put off by your daughter sitting quietly in the corner, observing?” Before her father could respond, the intercom buzzed.

“Mr. Geller,” his secretary said in her nasally voice. “Mr. Mariano’s here to see you.”

Alexander sighed. “Not one word Paris. You’re observing silently.” 

She nodded and moved to sit in the small chair in the corner. It was hard and slightly uncomfortable but she didn’t mind. It meant she would be able to stay focused.

Not a moment later, the door opened and in stepped Jess Mariano in all his suited glory. “Mr. Geller.” 

“I’m sorry, but who are you? I’m supposed to meet a very important client right now.”

Jess’ expression turned ice cold; tone of voice much the same. “That would be me. Jess Mariano, head of the Mariano Family. If you were expecting Jimmy, he’s no longer with us.”

Alexander blanched. “No longer with us as in…?”

“As in I put a bullet in him and he bled out in my office.” 

“Oh God…” He glanced to Paris out of the corner of his eye before looking back to Jess and swallowing. “P-please have a seat.”

Jess took a seat. 

Alexander patted at his face with his pocket square. “So...to what do I owe the pleasure of this visit?”

Paris sat there quietly, doing her best not to scream that she had known all along that Rory was dating a mobster and that she was wearing his locket.

“I’m here to talk business. Jimmy, frankly, was rather incompetent.” 

Alexander nodded. “Indeed. So what can I do for you? I can provide copies of all the paperwork, and explain what it all is. And if you’d like to revise the deal our companies have, I can put my lawyer in touch with yours.”

“That won't be necessary. I’ve already reviewed the paperwork. I’ve also had my lawyers draw these up. Most of our current deal will remain, with a few minor changes.” Jess laid the paperwork on the desk. 

“O-okay,” Alexander stuttered. Paris drew in a sharp breath. It was uncomfortable to see her father, always totally in control, afraid and cowering. Even stranger to see Jess, who had been very sweet in public with Rory, causing that reaction.

Jess smiled confidently. “I think we’ll get on quite well then.” He then cast his gaze over to Paris. “Paris.” 

“Mr. Mariano,” Paris responded blankly.

“I think it’d be in your best interest to cut the attitude with Rory.”

Paris flushed and looked down at her knees, unable to say anything.

“Paris,” Alexander said warningly.

Paris looked up and glared at her father quickly before swallowing and looking at Jess. “Duly noted, sir.”

“Good. Then I think we’re done here. My lawyers will be in touch with you.” Jess stood, elegant and poised. 

“I look forward to hearing from them,” Alexander said weakly. “Thank you for your generosity Mr. Mariano.”

“Have a good day, Mr. Geller, Paris.” Jess shook Alexander’s hand before heading to the door. 

As the door closed behind him, Alexander released a large breath he’d been holding and looked at Paris. “Let me guess. You’ve been copping an attitude with his girl.”

“It’s not my fault she’s so damn annoyingly present,” Paris snapped.

Alexander gave Paris the fiercest glare he could muster up. “No. More. You either be nice to her or you turn and you walk the other way. Do I make myself clear?

“Crystal,” Paris muttered. Damn that Rory Gilmore!

“Get out. Go home, I don’t care. I’ve work to do.” 

“Yes, sir,” Paris replied snarkily in a huff. Grabbing her coat and her bag, she stomped her way out to her car, and flopped herself down in the seat. Remembering that Tristan had asked for an update, she got out her phone and shot him a message. [Jess Mariano new Boss after coup. Rory off limits to mess with. -P]  
Tristan felt his phone buzz and pulled it out of his pocket. He certainly wasn’t expecting to read what was waiting for him. “Damn…”   
\----  
Rory thought her arms would fall off. Barely halfway through her shift at the diner and they were absolutely slammed, with tables being filled seemingly milliseconds after being vacated. “Luke I need two cheeseburgers with fries for table three and table seven just sent back their onion rings because they aren’t crispy enough,” Rory said as she dropped the offending plate on the counter and reached for the coffee pot. Before Luke could respond, the door opened and a delivery person stepped in, holding a floral arrangement. 

“I’m here for a Rory Gilmore?” The delivery man had a gorgeous bouquet of a dozen roses -- 11 were crimson and there was one white rose in the center. 

“T-that’s me,” Rory said, setting the coffee pot down and wiping her hands on her apron.

The delivery man handed her the bouquet and then the card. “From Mr. Mariano.” 

Rory took the bouquet and looked at Luke who shrugged. Shaking slightly, Rory set the vase, a beautiful thing of cut glass, on the counter and opened the card.

Rory:   
“If each day,   
each hour,  
you feel that you are destined for me  
with implacable sweetness,  
if each day a flower  
climbs up to your lips to seek me,  
ah my love, ah my own,  
in me all that fire is repeated,  
in me nothing is extinguished or forgotten,  
my love feeds on your love, beloved,  
and as long as you live, it will be in your arms  
without leaving mine.” -Pablo Neruda  
Love,   
Jess 

Rory raised a shaky hand to her mouth and stifled a sob. “Shit,” she muttered. A few heads turned and Miss Patty, who was sitting at the end of the counter, took the card from Rory’s hand and cleared her throat. Reading the card aloud, Miss Patty grinned at Rory.

“Well, well. That Jess is quite the romantic, dear. Quoted Neruda and everything.”

Rory blushed and wiped at her eyes. “Yeah.” Rory’s voice was wobbly and sounded small in the silence of the diner. Babette flashed Rory a huge grin; Luke was rather surprised by the whole thing.

With a sniffle, Rory smiled and turned to the roses. They smelled intoxicating and reminded her of gentle kisses along her collarbone. Gently, she picked the vase up and moved it into the store room.

Just as she stepped out, Lorelai stepped through the front door, bell jingling. “Why so quiet?”

Miss Patty handed her the card. “It came with a dozen roses-- 11 crimson and one white.” 

Lorelai raised an eyebrow at the older woman and shook her head before turning to the card. As she read, her eyebrows rose higher, her eyes got wider and her knuckled grew whiter. Looking up at Luke, she said, “Your nephew or not, the boy’s dead meat.”

“Oh, Lorelai. It’s romantic! The boy has class,” Miss Patty said nonchalantly. 

“Uh huh. Since when does class equate with sending my daughter a poem about sex?”

There was an audible gasp and everyone looked up to see Rory in the doorway to the storeroom. “M-mom!”

“Rory,” Lorelai said quietly. “We’re going to have a serious talk when you get home.”

Rory nodded and ducked her head before moving to get back to work. Clearing her throat gently to get her attention, Lorelai offered the card back. “Here.” Almost snatching the card from her mother’s hand, Rory stashed her treasure in her pocket and got back to work, grabbing the coffee pot and the new onion rings for table seven. The coming conversation would be none too pleasant.

Jess had just finished settling into his hotel in Hartford and was now halfway to Stars Hollow. He planned on surprising Rory -- hopefully she’d be free to go to dinner with him. No more than 10 minutes later, the gorgeous Thunderbird roared into town and parked in front of Lukes. Jess was still wearing the sexy tan bespoke suit. 

Rory was just finishing her shift, the smell of grease and coffee clinging to the black skirt and cream blouse she was wearing. Lorelai was waiting at the counter for her, to-go cup in hand.

The bell on the front door jingled as Jess stepped in. Once he was through the doorway, he removed his sunglasses. 

Rory looked up at the bell and a grin spread across her face uncontrollably. “JESS!” Throwing her apron at the counter, she threw herself across the diner into his arms.

Jess laughed and hugged her close. “Missed you, Booktease.” 

She snuggled into his chest. “I missed you too, Dodger.”

Lorelai cleared her throat and Rory instantly sprang away from Jess, blushing bright pink. “Sorry, Mom.”

“Oh, yea. Lorelai, these are for you.” Jess handed her a lovely bouquet of baby’s breath, gladiolus, and red tulips.

Lorelai accepted the bouquet warily. “You realize, of course, that I can’t be bought with pretty things except for diamonds.”

Jess smirked. “I’m aware. We’ll see about something like that for your birthday.” 

Lorelai raised an eyebrow. “You’ve got snark. Huh.”

Jess simply smiled and took a seat at the counter. 

“So to what do we owe the pleasure of this visit after sending my daughter a sex poem?” Lorelai asked.

“Mom!” Rory objected, resting a hand on Jess’ arm.

Jess sighed. “If You Forget Me is not a ‘sex poem,’ it’s a famous, heartfelt poem, it also went nicely with the flowers.” 

“Uh huh.” Lorelai nodded. “I remember analyzing that poem in high school. Sex is heavily featured if not outright the subject.”

“It’s a minor featured. The point of the poem is Neruda expressing his love to his beloved, and promising that for as long as she wants him, he will be hers and she will be his, for a lifetime, eternity, whatever. Yes, Neruda does have a lot of poems centered around sex, but If You Forget Me is not one of those.” 

Rory smiled at him adoringly, and Lorelai seemed shocked. “Well then.”

Jess shrugged. “I love literature...”

Lorelai shook her head. “No wonder she’s head over heels for you already. Anyway, what’s up? I didn’t receive any warning you were coming so…”

“I had a funeral Wednesday and have been away on business since Thursday. Today I had a meeting in Hartford so I thought I’d surprise Rory and take her to dinner, if that’s okay?” 

“Business? You’re seventeen. And I don’t know about dinner…”

“My father died of a heart attack Sunday, thus the company has fallen into my hands. While, yes, I am 17, legally I’m an adult. I’ve been emancipated since I was 15.” Jess played hurt really well.

“Oh I’m so sorry. If there’s anything Rory or I can do…” Lorelai trailed off helplessly. What did you tell a kid who’d been legally declared an adult at fifteen but had just lost his father?

“Thank you.” 

“May I please go to dinner, Mom?” Rory asked quietly, her eyes begging.

Lorelai looked between the two teenagers and sighed. “Sure. Just be home by nine-thirty.”

Rory squealed. “Thank you Mommy.”

Jess took Rory’s hand and followed her out to the car. 

“Thank you for rescuing me,” Rory whispered conspiratorially. “She’s trying to give me the talk again after that card you sent me.”

“How did she even get a hold of the card?” Jess unlocked the doors and slid into the driver’s seat. 

Rory slid into the passenger seat and waved at Lorelai who was watching them climb in with a sort of forced grimace, like she was just waiting to be in private so she could let loose and scream. Smiling, Rory said, “I sat it on the counter when I moved the flowers and she found it when she came in. Drive please, we’re torturing her.”

Jess turned the key and the engine roared to life, sounding every bit the hot rod it was. 

Lorelai squinched her eyes shut and Rory gently socked Jess on the arm. “Doofus. She’s already mad at us.”  
Jess laughed and pulled out onto the street, engine purring. 

Sitting back, Rory shook her head and grinned. “Alright now that you’ve tortured my mother, where are we going for dinner?”

“First we’re going to my hotel room so you can change.” Jess drove past the Thank You For Visiting Stars Hollow sign. 

Rory raised an eyebrow. “Change? Into what? I don’t exactly have clothes with me, Jess.”

“I’m well aware, that’s part of the surprise. I picked something up while I was in Chicago. I figured you could wear it to dinner.” 

If Rory hadn’t already been sitting back in her seat, she would have fallen back into it. “Jess you really shouldn’t have. And please tell me we aren’t going somewhere super fancy. I’ve been at work for three hours and I feel disgusting.”

“Rory. My room does, in fact, come with a shower.” 

She wrinkled her nose and stuck out her tongue for a second. “I know that. But I don’t have my makeup, anything to use on my hair. Hell, I don’t even have a toothbrush and toothpaste.”

“Rory.” Jess all but whined. “I’ve got all that covered. Lane told me what you used, so I made sure I had all that.” 

Rory blinked. “R-really?”

“Yes, really. And I’m going to take that stuff back and keep it at my place for when you visit.” 

Rory was dazed. “You...you mean, like, permanently?”

“Well, yea.” Jess said like it should have been obvious. 

“I don’t…” Rory stopped and cleared her throat. “I don’t know what to say.” Her words were pinched, like she was fighting back tears.

“Rory… I told you I was going to spoil you…” Jess replied gently. 

Rory nodded and took a deep breath. “I know...I just...I wasn’t expecting it so soon or this much at once and just…”

Jess reached over and took her hand, giving it a little squeeze.

Rory took another deep breath and returned the squeeze. “Sorry to freak out.”

“No need to apologize.” Jess smiled.   
\----  
Rory looked at the evening gown laying across the bed.“No. Jess, no. There is no way I can accept this. This is way too expensive.”

“You can, you will, and you must. It’s yours.” 

Between them on the bed lay a beautiful yellow gown, the skirt flowing over the bumps and ridges in the comforter. “Jess. Do not go all authoritative boss on me.” Rory glared. “There’s no way I can accept this. It’s designer for crying out loud.”

“Rooooooryyyyy!” Jess whined. “It’s yours, I got it for you. I would like to take my girlfriend out for a lovely dinner. I’d like to destress as well. If you don’t wear it, I’ll just keep it at my place and make you wear it to a formal gala, and I’ll buy jewelry.” 

Rory rubbed at her temples. “And we can’t just have dinner here? Relax and just spend time together? We have to go out? Also, that threat is not as terrifying as you seem to think.” 

Before Jess could answer his phone rang -- it was GQ asking if he could do the interview. Jess mentioned dinner with his girlfriend and they were more than willing to accommodate. The call ended quickly as it came.   
“Did you just…” Rory said quietly, her tone clearly angry. “Ohhh no. No, nope, sorry, not going.”

“I’ll read The Fountainhead.” 

That stopped Rory dead in her tracks. “Are you...trying to bribe me? Jess!”

“Yes. I’ll read Atlas Shrugged too.”

Rory looked him dead in the eye. “You swear on my life?”

Jess held out a pinky, knowing full well how important pinky promises were in the Gilmore family.   
Rory hooked her pinky with his and gave it a squeeze. “Fine. But I expect full book reports on my desk in two weeks.”

Jess made a face but agreed. 

Grabbing the dress, Rory headed towards the bathroom. “And maybe if you’re really good you’ll get a reward.”

Jess lit up at that. 

Rory rolled her eyes and grinned before closing the bathroom door and sighing. Rushing through a shower, she wrapped up in a fluffy white complimentary robe before starting her hair and makeup.

Jess read one of his books while he waited, pausing only to adjust his hair. 

A little while later, Rory stepped out of the bathroom with her dress on and her work clothes in hand.   
“Okay…” she muttered. With a concentrated look on her face, she dropped the bundle of clothes into the desk chair and stopped at the mirror to mess with her hair a bit. “Alright. Shoes…” Continuing to mutter, she moved about the room, mostly ignoring Jess as she finished pulling herself together.

Jess watched her as she moved around of course. 

Finally, Rory stood still in the center of the room, looking slightly lost. “I’m out of things to do,” she said, anxiety tingeing her voice slightly. Jess closed his book and stood up. 

He straightened his suit and made sure his hair looked okay before taking Rory’s hand. “To dinner then.”   
She nodded, eyes terrified. “To dinner…”

Jess led them out to the car and headed further into downtown Hartford. He’d made reservations at ON20, a trendy 5 star place. 

Rory fought zoning out in terror. “So where are we going?”

“We’ve reservations at ON20.” 

“Oh,” she said quietly. For a second she said nothing and then, “Jess that place is expensive.” Her voice was tiny.

“Mhm. Not as expensive as some of the places I could take you in New York.”

She closed her eyes and focused on breathing. “Jess…”

“Rory, Booktease. Please try to enjoy this. Look, it won’t be a thing we do often, but I fully intend on taking you to places like this on occasion. You look absolutely stunning. You have nothing to worry about, okay?” 

“I just...new situation, new clothes...anxiety.”

Once the car was parked Jess leaned over and kissed her cheek, taking her hands in his. “It’ll be okay.” 

Rory nodded and blew out another breath. “I know. And I’m trying. Honestly.”

“It’s just another adventure.” Jess kissed her lips, soft and gentle. 

“You’re gonna smear my lipstick,” Rory murmured.

Jess pulled back, grinning. “Come on.” He headed around to her side and opened the door for her.   
Taking the hand he offered, Rory climbed out of the car and grabbed her small purse from the floor before shutting the door.

Jess walked up to the hostess at the entrance. “Table for 3 under Mariano.” 

The young lady checked her book and grinned. “Right this way, Mr. Mariano, and may I just say you both look lovely this evening.” Jess grinned and Rory blushed. “Thank you,” Jess replied.

The hostess smiled and handed over two menus. “You’re welcome. I’ll escort your third party member when they arrive.”

Jess nodded and pulled out Rory’s chair for her. They glanced over the menus and a few minutes later, the journalist arrived. 

The hostess led the journalist over. She was a young, 20-something blond. Her name tag said Cally Stephens. “Mr. Mariano.” She smiled and Jess shook her hand and pulled out her seat. “I’m Cally, I’ll be doing the interview. And who is your gorgeous companion?”

Rory blushed. "I'm Rory Gilmore."

Cally grinned. “It’s a pleasure to meet you both.” 

Rory smiled weakly. "Pleasure's all mine." God this journalist was pretty. And she threw Rory seriously off kilter.

Jess ordered his and Rory’s drinks when the waiter came around. He also said to put Cally’s on his bill as well. 

"Well well. I can't say that's ever happened before," Cally said. She was clearly trying to refrain from an outward show of excitement.

Jess smiled cordially. “Then you must’ve only interviewed assholes. A gentleman never makes a lady pay for her own.” 

Cally's smile widened for a second before she shook her head. "Well then. Shall we get down to business or shall we wait for drinks before I begin the interrogation?"

Her question was answered for her as the waiter set their drinks down. 

"Excellent! So...to start, are you alright with me recording this interview for future reference?"

“That’s fine.” 

Cally pulled a recorder from her pocket and murmured the date, time and title of the interview, before indicating Jess had given permission for her to record, then setting the device on the table and looking at him, suddenly very serious. "So, Mr. Mariano. What is it like to suddenly be head and owner of a multinational corporation at only 17?"

“It’s not that much different from what I was doing before to be honest. Jimmy always had me in a high responsibility position within the company. While I learned a lot from watching him, I also learned what not to do in order to make us more successful. And I think our current percentages show that.” 

"And by Jimmy you mean your father, recently passed James Mariano, who was responsible for extending the company's reach abroad yes?"

“Yes, that’s who I’m referring to. We weren’t exactly close, but family sticks together.” 

Cally nodded. "And what sort of legacy is he leaving you, beyond extending the company's reach? Is the company in good shape? Will you be able to improve it even further, perhaps earning it the label of international?"

“The company is in the best shape it’s been in in years to be blunt. As for it becoming international, I’ve no doubt that it will. I have a meeting with the Euro 5 next week, finalizing our contracts and I have to be in Dubai directly following.” 

"So you haven't faced any opposition on those two fronts? There are some that have voiced doubts as to your qualifications to run the company. Is it true that you became an emancipated minor at fifteen?"

“To answer your first question, no I’ve not faced any opposition and any I may or may not encounter in the future, I’m sure will be resolved accordingly. As for the second, yes, that’s correct. I was emancipated at fifteen. Regardless, I’ve already graduated high school, speak five different languages and have run a majority of this company since I was fifteen. I am more than qualified I think, should anyone still doubt that.” 

Cally was obviously impressed. "I should say so. And what of the rumors that you and your father had a volatile relationship, and that your emancipation was a result of that?"

Jess took a sip of his drink. “Why I was emancipated doesn't matter. It's a legal matter, nothing more. True, we may not have had the best father/son relationship. But my emancipation was something we both agreed on. It didn't serve to change my life much except allowing me to do proper work on the company.”

"I appreciate your openness and honesty." The waiter came to the table and the conversation paused as dinner orders were placed. As soon as the waiter was gone, Cally was back on the war path. "There are rumors your father had ties to the mafia, organized crime. Care to comment?"

Jess laughed good naturedly. “Honestly I find it quite stereotypical and rather funny. An Italian family is always accused of having Mafia associations. It’s textbook.” 

Cally laughed and nodded. "Indeed. So." She turned to look at Rory. "Rory. What's your relationship to Jess?" Jess reached over and held Rory’s hand. 

"I'm his girlfriend," Rory said quietly.

Cally smiled brightly. “And how did you to meet?”

"I went to see Phantom of the Opera on Broadway with a group from school and Jess had the seat next to mine." Rory was saved for a few seconds by the arrival of the food but soon, Cally was back at it.

Jess smiled fondly. “She was reading one of my favorite books, Howl & Other Poems by Allen Ginsberg. We bonded immediately over our love of literature.” 

Cally smiled. "Ah a literary couple! So how long have you been together?"

Rory looked at Jess. "It's been....?"

“Almost two months.” 

Cally was clearly impressed. "I would have assumed much longer. You two have the whole "he moves I move" thing going."

Rory blushed but smiled up at Jess. “Our friends have said that too.” 

"Oh really? Why do you think you're so close?"

“We just..click. We’ve a lot in common-- books, music, but I think it’s the fact that communication just comes so easy to us. We’ve never had to struggle to make conversation, it’s been like that since the beginning.” 

Rory nodded. "It's always been simple."

Cally nodded appreciatively. "And what about your family Rory? Do they approve of Jess? Have they met him yet?"

“My mom really likes him, I think. She's met him twice now, and so far hasn't tried to kill him so...other than that, my grandparents and dad haven't met him yet."

Jess grinned at her rather shamelessly. 

"That's...better than I expected when I heard two months. Alright, I'm done torturing you, I promise."

The rest of the dinner went by wonderfully. Jess paid the bill and then it was photo time! “Alright, I’d like two photos, one of you both together, and one of Rory.” 

Rory froze. "Oh no really. I'd rather not."

“Rory, darling, you look stunning.” Cally gushed and motioned Jess to put an arm around Rory. They looked breathtaking together. 

Rory tried to relax. "These aren't gonna get published are they?"

Cally took the picture before answering. She gasped a bit as she reviewed it. “You look...wow…” She showed them. “Of course I’m publishing that.” 

Rory blushed. "I just...I'm just not sure I want my picture published in such a...high profile way."

Jess turned to Rory and spoke quietly. “It’s just one picture. It’d be certain to, what was it? ‘Keep any New York pretty girls away,” Jess teased good-naturedly. 

Rory glared a bit and finally conceded with a slight nod of her head. "Fine. But you," she pointed at Jess, "get to tell my mother!"

“Will do.” 

Cally beamed and took a few more pictures, including a solo one of Rory. 

When she was done, Cally smiled. "Thanks Rory. I'd love to do a solo shoot focused on you sometime. Maybe in something less...conservative?"

Rory blushed and smiled shyly. “M-maybe.”   
\----  
Jess opened the door to his hotel room and led Rory inside once more. 

"Oh thank God," she muttered, walking in and collapsing onto the bed.

Jess joined her. “We’ve an hour and a half.” 

"I hate you," she mumbled into the pillow noncommittally.

“You love me.” Jess slid his arms around her.

"Well right now I hate you," she mumbled again. "You didn't tell me that was coming."

“I was a bit surprised myself, I thought they’d gotten all the photos they needed earlier today.” 

She snuggled closer to him. "Next time, a warning would be wonderful. For all of it. I appreciate that you wanted to surprise me but this was all a little much."

“Noted.” Jess kissed her cheek. 

Rory smiled gently. "Dinner was good, though that reporter really threw me off..."

“How so?” 

Rory shook her head and looked up at the ceiling. "Just sort of like...I don't know. Her smile was not the normal smile women give each other."

Jess actually started laughing. “Rory…she was attracted to you. Cally’s most likely bisexual.” 

Rory started and looked at him, clearly shocked. "Okay but who in their right mind would pay me any mind when you're right next to me in that suit?"

Jess grew serious really quick and locked eyes with hers. “Rory. You’re beautiful. And tonight? In this dress… you took everyone’s breath away.”

Rory leaned up on an elbow and started straightening and smoothing out his lapels, not making eye contact. "Okay. For arguments sake I'll roll with that. But still, focusing on me when next to me is you -- gorgeous no matter what but three times as gorgeous in this suit," she looked up at him from under lashes, "is crazy."

Jess responded by kissing her a bit roughly.

Her arms crept up around his neck and one of her hands started pulling at his hair, just a little bit.

That of course elicited a soft moan from Jess. 

"Jess," Rory sighed breathlessly. "We really shouldn't..."

“That doesn’t sound like a no…” 

"When have I ever been able to tell you no?"

“Mhm...if you really want to stop I will.” Jess pressed a kiss to her neck. 

Rory gasped. "No fair"

“All’s fair in love and war.” Jess bit down lightly. 

"Mm..." Rory tugged at his hair. "Not where Mom could see," she said noncommittally.

“Fine.” Jess moved lower, towards her collarbone. 

Rory groaned. "You tease..."

Jess, living up to that, stood up and slowly took off his suit coat. 

Propped up on an elbow, Rory watched as he started stripping for her. "You don't have to make me fall in love again just yet."

Jess smirked and worked on tugging his tie off. He never once broke eye contact. When Jess moved to his shirt, he made a show of going slow. 

Rory braced herself on both elbows and watched her man, her Jess, strip for her. "On second thought, maybe I need a reminder. And I still owe you a reward for good behavior," she murmured, entranced.

Jess flashed her a smile while he tossed his shirt to the chair and then started to undo his belt; he pulled it off in one swift movement.

It felt like she'd lost her breath. Even though she'd seen him naked before, had pulled his clothing off in desperation, there was something...almost too much about his stripping.

Jess undid the button on his pants and pulled the zipper down. He stepped out of them and had them on the chair in a matter of seconds. 

"Okay maybe it is a good thing I'm in some of those pictures."

Jess laughed softly and joined her on the bed. 

"What, not stripping all the way? That's bogus no tips for you," Rory joked, pulling him to her so that their foreheads touched.

“I figured I’d do that next time.” Jess leaned down and kissed her, silencing anything else she might have said. 

She sank into the kiss, which was sweet if a bit rough, and her fingers splayed across his chest and in his hair. "I love you," she whispered into it.

“Love you too.” 

"Help me out of my dress?"

Jess sat up and helped her unzip it. 

Standing, Rory slipped off her shoes and let the straps of the dress slide down her arms as she stepped out of the dress, letting it pool on the ground. Leaning over so that she could look Jess in the eye, she bit her lip and whispered, "Thanks."

Jess’ pupils were blown wide and his hair was deliciously messy. “You're welcome.” 

She pressed a gentle kiss to the corner of his mouth.

Jess’ breath hitched ever so slightly. 

Rory chuckled. "I love that I can make you react that way." Her voice was gentle, her breath a whisper across his warm skin.

Jess blushed a rosy color. 

Gently, she took one of his hands and pressed it to her sternum, where her heart beat an accelerated but steady pace. "Jess, I want you."

Jess tangled his fingers in her hair and kissed her near breathless. He gently flipped their positions so he was now on top.

Rory hitched a leg upwards over his hip, her nails scratching at his back gently.

Jess failed rather miserably at keeping silent when she did that.“Nemmeno immagini cosa ho intenzione di farti…” 

"Translation?" Rory asked breathlessly. The Italian was sexy but she figured knowing what it meant would be even sexier.

“You can’t even imagine what I’m going to do to you…” his voice was husky and rough. 

She gasped loudly. "I was right. Even sexier when I know what it means," she muttered before kissing him. Hard.

Jess slid his arms around her, wanting to be as close as possible. 

Rory's other leg wrapped up and around his hip, muscles tensing as they fought to get as close as possible.

Jess moaned and rolled his hips, half hard already. 

With a small gasp, Rory nipped at his lower lip and then started kissing down his jawline.

“Fuck, Rory…”

Rory grinned and said, "Whatever are you talking about, Mr. Mariano?"

“Maybe I’ll just show you instead.” Jess slid his hands to her hips and swiftly tugged her panties down and off. 

"A wonderful idea," she responded breathlessly.

Jess wasted no time in sliding a finger into her; making sure to go slow and keep track of her reactions. 

She gasped and froze for a second before her hips rolled. "Fuck," she whimpered.

Jess took that as initiative and set a steady, almost teasing pace. 

Rory whimpered again and one hand moved towards his crotch, lightly brushing against his half-hard cock. "Two can play that game."

Jess bit his lip to keep from moaning. “Damn, Rory.” 

"Jess, I wanna hear you," Rory murmured, repeating what he'd told her the night she'd visited him in New York.

“You will.” Jess pressed a kiss to her lips and added a second finger. 

Rory's breath was shaky and she returned the kiss slightly desperately, before moving on to kiss and nip at his neck. "Good. Because like I said, I love that I make you react that way."

Jess’ eyes fluttered shut momentarily as he made a pleased sound.

Her hand grew more insistent for a moment before she tugged at the waistband of his boxers. "Off," she demanded huskily.

Jess slid his fingers out of her and momentarily sat up to slide his boxers off and toss them away. 

"Better." Bringing his face to hers, Rory kissed him soundly.

Jess kissed her rough and needy. 

"Jess...." Rory made a slightly frustrated sound. "Fuck."

Jess trailed kisses along her jawline. “Rory,” he replied, voice rough and accent thick. 

"Oh God..." she muttered. "I want...." She huffed. Words were failing her. Miserably.

Jess got the gist of what she was trying to say and grabbed a condom from the bedside table. He tore open the package and quickly got it on. 

Desperate kisses were trailed along his neck, his shoulder, his jaw. Rory was surprising herself with how much she wanted this, wanted him.

“Rory...f-fuck...need you.” Jess managed to get out between moans and soft pleased sounds. 

Her legs wrapped around his hips and pulled him closer. "Please, Jess. Please."

Jess positioned himself, and slowly slid into her. “Rory, You’re so perfect…” 

Rory buried her face in his shoulder for a second, feeling the need to breathe and adjust. For a moment, it was overwhelming, and her breath hitched just a bit.

Jess murmured sweet things to her as she took a bit to adjust. 

Gently, she pressed a kiss to his cheek and nuzzled at his neck. "Jess..."

Jess slid out of her, just to thrust back in not a second later and repeated. He made sure to go slow at first, not wanting to hurt her. 

Rory's eyes drifted shut and she moaned, hips moving to meet his as she pulled at his hair.

Jess’ breath hitched and he moaned rather filthily. He really did enjoy a bit of rough. 

Her nails raked his scalp and she bit her lip. "Ohh God."

Jess’s hands slid down to her hips and he set about marking her thoroughly. 

"Jess, just fuck me already," Rory whined. "I'm not gonna break." She nipped at his neck, planning to leave her own marks.

Jess did as he was told and moved significantly faster and harder, his nails leaving shallow crescent moons on her hips. 

She moaned again and latched onto his neck, marking her territory. She scratched at his back, her touch losing any sense of gentle.

“Rory!” Jess cried, not even trying to be quiet at this point. 

Rory grinned for a second before she groaned. "Oh God, Jess."

Jess kissed her, almost bruisingly, occasionally nipping at her lips.

Rory's legs tightened around his hips, wantonly trying to pull him closer. Her fingers tangled in his hair again as she lost herself in the moment.

Jess fucked her into the mattress, so that the headboard banged against the wall and rattled the picture frames. 

With a breathy moan, Rory pressed a kiss to his shoulder.

Jess locked eyes with Rory’s; his were the color of black coffee. “Rory...” 

The eye contact and her name, said in a voice drenched in sex, pushed the tension slowly building in Rory to the tipping point. "Jess..." Her voice was tight with need. "I'm..." Her breath caught in her throat.

“I got you…” Jess pressed a kiss to her pulse point. 

"Jess!" In the space of a millisecond, she was falling from the peak, her whole body trembling as the world exploded and reassembled itself. 

Jess saw white as she clenched around him, “Cazzo, Rory…!” A few other expletives and sentiments of love tumbled out as he lost control and then came down from his high. 

Rory smiled at him as she tried to catch her breath. "Wow."

Jess smiled, looking every bit as wrecked as she did. He took a moment to slide out of her and toss the condom in the bin before cuddling up to her once more. “I don’t even have words...”

With a yawn, she curled into his side, one hand draped across his chest. "You can say that again." She blushed. "I really hope the people next door were out..."

Jess laughed a bit. “If not, they got a nice show.” 

She buried her face in the crook of his neck with a mildly distressed moan. "Oh God."

Jess kissed the top of her head. “Love you.”

There was what sounded like a mumbled "I love you too" and then another yawn.

Jess set an alarm on his phone for 10 minutes in case they fell asleep. 

"Jess?" Rory asked after a few minutes.

“Mhm?” Jess’ eyes were still closed. 

"That wasn't..." She made a frustrated little noise at her inability to articulate what she wanted to know. "God dammit."

Jess opened his eyes. “Rory?” 

She shifted position a bit, trying to get into a spot where she could formulate her thoughts. Finally deciding to toss tact out the window, she looked up at him and asked, "That wasn't your first time was it?"

Jess bit his lip and shook his head. “No, it wasn’t…” he replied rather quietly. 

Rory nodded and snuggled closer. "Thanks for being honest," she mumbled, her tone light and happy.

“Wish it had been though.” Jess hugged her close. 

"Well that's very sweet, but I appreciate that you know what you're doing."

Jess smiled. “As much as I don’t want to, we need to get dressed…”

Rory groaned and snuggled even closer, eyes squinched shut. "Don't wanna," she mumbled. "Don't wanna face Mom..."

“But we don’t want to be late either.” Jess ran his fingers through her hair, smoothing it down. 

With another groan, Rory pulled away and looked at the clock. "I'm so sick of always getting pulled away from you," she muttered. Getting up, she searched for her underwear amidst the pile of clothes scattered across the floor.

Jess agreed wholeheartedly, and grabbed his boxers and tugged them on before grabbing his button up. He was dreading the meeting with Lorelai, and even more so, having to say goodbye to Rory.   
\----  
They pulled up to the house at 9:31, only to see Lorelai peering out the window through the curtains. "We're dead," Rory mumbled.

Jess ran a hand through his hair. “We’re only a minute later though?” He shut off the car and got out. 

"A minute later, and we clearly look like we've been up to something." Rory slowly got out and nearly jumped back in the car when she heard the front door open.

"What happened to back by 9:30?" Lorelai asked expectantly.

“We were only a minute late.” Rory pointed out.

Lorelai gave her a look that clearly said she was not impressed. As she walked closer, it was easy to see she was clearly taking note of ruined hair, rumpled clothing, and, the coup de grace, a couple of large hickeys on Jess' neck. "Rory?" she queried.

Rory didn’t catch on right away, forgetting completely about all the marks she’d left on Jess. “Yes?”

"You wanna explain the hickeys all over your boyfriend's neck? Or should I start extrapolating?"

Rory paled a bit and clutched onto Jess’ sleeve to keep herself steady. “U-uhm…”

Lorelai looked at her hard. "Jess," she said calmly. "I think it's time for you to say goodbye for the evening. Feel free to come by for your half of this interrogation, indictment and trial tomorrow though. Rory, inside."

Jess gave Rory a chaste kiss. “Love you.” he whispered in her ear before he walked back down the front steps and got in his car. 

Lorelai held the front door open as Rory dejectedly made her way inside. As the front door closed behind them, Lorelai pointed to the couch. "Sit." Before she could see if Rory did as she was told, she went to the kitchen, needing coffee. 

Rory fidgeted with her sleeves as she waited. 

A few seconds later, Lorelai returned, mug in hand. Sitting down across from Rory, she stared at her for a few seconds, watching her squirm before going to take a sip of her coffee.

“We were safe!” Rory blurted out. 

Lorelai choked a bit and spluttered. "Good Lord, child," she coughed. When she'd recovered, she looked Rory in the eye. "How safe?"

Rory blinked. “Condom.” what other way was there? She didn’t have birth control yet.

Lorelai closed her eyes and sighed. "We're gonna get you birth control..." she muttered. Louder, she said, "Rory, do you understand why I'm upset?"

Rory nodded. “C-cause I didn’t tell you before it happened?” 

"No. Well, kinda. But I'm upset because you don't seem to have thought ahead. Condoms, wonderful as they are, fail. And what if he hadn't had one? Jess seems like a very sweet kid, but what is he gonna do if you end up pregnant? He's got a business to run." Lorelai took a sip of her coffee. "You get to make your own choices, but you should learn from my mistakes."

Rory frowned. “We already talked about that! He’s more than capable and willing to take care of me should anything happen. But it won’t!” 

Lorelai blinked and felt her eyebrows rise. "Wow. Such confidence. Rory, you're only 16. And sex is a very important step in a relationship. It can't be used to save something, only cover the cracks or strength the struts."

“I know that! We know that! We didn’t just think, ‘Hey, sex would be a great way to pass the time!’ We did it because we love each other!” Rory’s eyes were getting blurry with unshed tears. 

"Rory it's been two months! Love does not..." She trailed off, remembering her brief, but brilliant, time with Max. "You love each other?"

Rory nodded, finally breaking, tears running down her cheeks. “Yes we do, and tonight wasn’t the first time we said it.” Her voice wobbled. 

Lorelai felt guilty. Putting her coffee cup down, she moved to sit next to Rory and pulled her into her arms. "Well at least there's that." She kissed the top of her head. "I'm sorry to be so hard on you," she whispered.

“I didn’t wanna cry! I was so happy about tonight.” Rory sniffled and wiped her eyes on her sleeve. 

"And I'm so sorry to make you cry," Lorelai said gently. "Would it make you feel better to tell me about it? In as little or as much detail as you like."

Rory nodded. “Can I have coffee first?”

"Sure, kiddo. Kinda surprised you're awake as is, to be honest." With one last kiss to Rory's forehead, Lorelai got up and made her way to the kitchen for another cup of coffee. It took her a minute, and the whole time, she couldn't stop hoping and praying that her baby had not had a horrible first time. Returning and handing Rory her cup, she grabbed her own and curled up on one end of the couch.

Rory took a sip before she began. When she looked back up she was grinning. “It was absolutely mindblowing! Like, I couldn’t have imagined it being better!” Rory blushed a cute rosey color. “Mom. He stripped for me.” 

Lorelai sputtered into her coffee again. "He stripped?! Wow. Just...wow. Not his first time at the rodeo, huh?"

Rory grinned and shook her head. “I couldn’t take my eyes off him! And he just...he teased and took forever unbuttoning his shirt.” 

Lorelai grinned. "The way every good stripper should."

Rory looked a bit sheepish, but still pretty smug when she said the next part. “We made the headboard hit the wall and the picture frames rattle; I’m surprised we didn’t get a noise complaint.” She took another sip of her coffee. 

Lorelai sat there, frozen. Her jaw was on the floor, her eyes wide. "I...."

Rory mustered up the most innocent smile she could. 

Lorelai snorted. "Uh uh. That smile ain't gonna fly. Not tonight." She looked Rory in the eye and asked, "And he took care of you?"

“Very much so. He was a perfect gentleman.” She blushed again. “I was probably rough on him… I uhm… left quite a few marks.” 

Lorelai squinched her eyes shut and shook her head lightly. "So I saw."

Rory giggled. “His back is worse.” With that she stood and went to refill her coffee cup. 

Lorelai drifted after her. "Nails?"

“Yep.” Rory came back and resumed her spot on the couch. 

"And what about you? You got hickies and marks covered by makeup?"

Rory tugged her shirt collar down. “Made sure he didn’t make them where everyone could see.”

"Smart. Much smarter than I was."

Rory laughed. “But really, it was perfect night. And you’ll never guess where he took me for dinner!”

"Where?"

“ON20!” 

Lorelai gasped. "He didn't!"

“He did! He really did! Mom oh my god the food was heavenly. And the zaggat gave it a three dollar sign rating! It’s 5 stars!” 

Lorelai sat back in shock. "That boy is rolling in it." She looked closer at Rory. "You didn't wear your work clothes there did you?"

Rory shook her head. “No, I wore this really pretty yellow evening gown.” 

"Let me guess. Jess bought it for you?"

Rory nodded. “He even called Lane for assistance.”

"That boy...." Lorelai said quietly. "He's...well he's a lot better than Christopher that's for sure."

Rory hugged Lorelai. 

Lorelai smiled and returned the hug. "I'm glad you're happy. But in all seriousness, hold off until we get you some birth control, yes? Just for my peace of mind."

“I promise.” Rory held out her pinky. 

Lorelai hooked her pinky with Rory's and grinned. "Thanks kid. You know, you're probably the best kid I could have gotten."

Rory beamed. “Love you, mom.” 

"I love you, too, Rory. Now go get ready for bed. Let Jess know you're not dead or under house arrest."

Rory smiled and all but skipped to her room. She closed the door behind her and took out her phone. [Everything is fine now. -R]

There was a moment of silence before her phone buzzed with an answer.

[Good to hear, Lorelai looked ready to kill. -J]

[She was. But it was mostly a misunderstanding. You coming by tomorrow? -R]

[Yea, What time? I’ve got the day off. -J]

[Whenever, really. I did promise no more sex until I have pills, btw. -R]

[Meet for breakfast at Luke’s then? And okay, we’ll manage. -J]

[Depends on what time you mean. Earlier than 9:30 is pushing it with Mom. It'll help that we're in different cities. -R]

[10:30 good then? -J]

[Should be :) You'll come sans weapons right? -R]

[Ish. I will have a switchblade in my boot. -J]

[Okay well that's explainable. Guns not so much. -R]

[Well, I’m not expecting to need a gun in SH, It’ll remain locked away in my trunk. -J]

[I appreciate that. A lot. -R]

[Get some sleep, I’ll see you tomorrow. Love you. -J]

[Love you too. Make sure you remember the music. -R]

[Will do, I’m thinking Metallica. -J]

[Your neighbors are gonna hate you lol -R]

[No fucks given. -J]

[As per usual. :) anyway, good night. I love you, I'll see you tomorrow morning for a very difficult day. -R]

Jess smiled and set his phone on the bedside table. He then burrowed under his covers and was asleep in seconds.

**Notes for the Chapter:**

> Nemmeno immagini cosa ho intenzione di farti-- you can't even imagine what I'm gonna do to you


	10. I Want You: part 2

**Notes for the Chapter:**

> I am sooooo sorry for the delay updating. Things got really crazy in my life for a while, but things are going better now and updates should be more frequent. :) Thanks for your patience.

Rory sprang through the door to Luke's at 10:25, her smile bright and expectant.

Jess was noticeably dressed down today-- jeans, tshirt and his favorite leather jacket. He and Luke were chatting as Jess made some more coffee; neither had noticed Rory yet.

Quietly, Rory walked up behind Jess and tapped one shoulder before moving the other direction, failing to stifle a giggle.  
Jess turned around and saw a blur of brown hair. “Rory?”

"Boo!" she said, dying of laughter.

Jess grinned and pulled her into a hug. “Good morning to you too.”

Snuggling into his arms, Rory sighed happily. "It's good now."

Jess kissed her cheek. “Go sit, I’ll bring you coffee.”

"Such a gentleman." Rory pranced away to a table, Lorelai following her as she came through the door, waving a hello to the guys.

"She ran off and left me."

Jess grabbed a second coffee cup and filled them both up. “Luke’s busy, so I’ll be taking your orders.”

Rory tilted her head. "You pulling a shift? That's something I never thought I'd see."

“You know I can cook.”

"Well yeah."

Luke called Jess back to the kitchen right as Jess was about to respond. “Back in a sec.”

Rory nodded and looked at Lorelai. "If he didn't already own a multinational corporation, I'd be worried he was gonna put me out of a job!” 

Lorelai laughed. "Yeah well be grateful kiddo." 

Jess came back a few minutes later, “Okay, what’ll it be?” He took his notepad out. 

"I'll have the pancakes, with a side of bacon," Lorelai said. 

"Two chocolate muffins and are you not eating with us?" Rory asked, concerned. 

Jess flashed her a smile. “I’ll be eating with you, I’ve been working since he opened at 5am.” 

"Been busy then?" Lorelai asked. 

“Yea, plus we got in the week’s shipment.”

"Yikes," Rory said quietly. Shipments meant some juggling when the place was busy.

Jess went back to the kitchen to bring their food out. His and Rory’s was easily gotten, Lorelai’s was mid-cooking.

"Thanks babe," Rory said when he sat her muffins down. 

Jess took a seat by Rory. 

"And where's mine?" Lorelai asked.

“Luke is still cooking yours, said he’d bring it out in a few minutes.” 

Lorelai hmpfed good naturedly. "I swear he does it on purpose." 

“I do not.” Luke set Lorelai’s plate down a few moments later.

"Uh huh. Suuuure you don't," she said, grabbing a piece of bacon and taking a bite. 

“By the way, be ready at 7, I’m taking you to dinner.” with that Luke headed back in the kitchen. 

Lorelai choked a bit. "Wait WHAT?!" She tossed her bacon strip down on her plate and got up to chase after him. "Did I just hear what I thought I heard?" 

"Well that went well," Rory said as she took a sip of her coffee.

“You’re welcome.” Jess grinned and took a sip of his coffee. 

"I appreciate you convincing him," Rory said, breaking open a muffin as they listened to the sounds of yelling, followed by clattering dishes, more yelling, and then a suspicious silence. "Want a bite?" 

“Yes.” 

Rory broke off a bit of muffin and held it out towards him. "Open."

Jess opened his mouth. 

Rory popped the bit of muffin into his mouth. As she withdrew her hand, Lorelai drifted back out into the dining room, looking slightly dazed. "He's taking me to dinner," she murmured. "I have nothing to wear..." 

“He likes that blue dress you wore to some Dragonfly dinner thing,” Jess piped up after he swallowed the bit of muffin Rory gave him. 

Lorelai nodded, still on a high. "Rory, we'll have to...do my hair." She took a bite of bacon. "And, and find the shoes..." 

"We will Mom," Rory said gently, fighting to hold back laughter. 

“Oh, and before I forget, Rory’s gonna be in the new issue of GQ with me.” Jess finished his toast. 

"What was that?" Lorelai asked dreamily. 

“Rory’s gonna be in the new issue of GQ with me, hits stands tomorrow.” Jess stood and grabbed Rory’s hand, wanting to make their escape. 

Lorelai blinked and seemed to come back to herself. "She's gonna be in GQ with you? When did this happen?" 

Jess looked towards Rory. “After we had dinner.” 

Lorelai looked to Rory. 

"It sort of got sprung on us. The lady doing the interview was...well Jess said she was trying to hit on me, but I really don't know." 

Lorelai looked back to Jess. "Was she hitting on her?" 

“I wouldn’t say hitting on her, but she was definitely attracted to Rory.” 

Rory shook her head. "I still say no, but whatever. She wanted a shot or two of us together for the spread. Which, by the way, you," she said, poking Jess in the ribs, "never told me what it was officially for." 

“GQ’s 30 Under 30 Business Edition. I uh...made #1. So I got a four page spread and the cover.” 

Rory looked rather smug and Lorelai's jaw hit the floor. "Of course you did," Rory said proudly. 

Lorelai shook her head. "Number one on a GQ 30 Under 30 list and my daughter happens to be dating you, and is in your photo spread, no biggie." She was slightly breathless and sounded anxious.

Jess looked a bit shy but tried to play it off. “I wasn’t expecting it either, but I got a call while I was in San Francisco.”

"San Francisco? Were you there on business?" Lorelai asked, cradling her coffee in her hands.

“Yea, I had meetings scattered out. Just finished up in Hartford yesterday. I had meetings in Chicago, Los Angeles, Las Vegas, San Francisco, and Hartford. This week I have a meeting in London with the Euro 5 and in Dubai directly following.” 

Rory glanced at him while Lorelai nodded appreciatively. "So what does that mean for you and Rory?" Lorelai asked quietly, her tone carefully neutral. 

“It shouldn’t have much of an effect. I just took over the company; right now I’m securing contracts and meetings with clients. That should be wrapped up by this week, then I’ll be working solely out of New York and occasionally Hartford.”

"So you wouldn't normally be the one going to these meetings? Your job as head of the company is much more stationary?" Lorelai clarified. 

Jess nodded. “I’d only have to travel a few times a year for meetings once everything is wrapped up. If they happened to fall during a break or holiday Rory, you, and Luke would be more than welcome to come along. I fly privately.”

Lorelai's eyebrows flew up. "Privately as in private jet privately? Wow. You've got serious money kid." 

“Yea...private jet. But I didn’t have much access to any of this 'til recently. Jimmy was a selfish bastard. I grew up in dingy apartments in less-than-stellar neighborhoods. My high school was an absolute shithole.”

Rory grabbed Jess' hand and gave it a squeeze.

Lorelai cradled her coffee cup in her hands. "Huh. I never would have guessed.”

“This is where I used to live.” Jess took out his phone and pulled up a picture of the sorry excuse of an apartment building he used to live in. 

Lorelai looked at the picture and shuddered. “I’m glad you’re out of there, kid. But where do you live now?”

“One MiMa Tower in the Midtown/Hell’s Kitchen area of Manhattan.” Jess pulled up another picture. 

Lorelai choked on her coffee a bit as her eyes bugged out of her head. “Good lord.”

Rory piped up. “He has the penthouse level.”

Jess shot Rory a look of faux betrayal. 

Lorelai’s eyes squinched shut and she pressed a hand to her forehead. “That’s where you’ll be if you ever go visit him in New York?” Lorelai asked quietly. “And there aren’t even neighbors to keep you two decent.”

“I have a guest room.” Jess offered. 

Lorelai sighed. “I’m just gonna pretend I don’t know anything anymore.”

Rory took that as their cue to leave and led Jess out of the diner.  
\----  
Rory and Jess had decided to go to the bridge for the afternoon, more to distance themselves from the frantic energy that was Luke and Lorelai than anything else. "I almost regret setting them up," Rory mused. "I mean, it's about time but the accompanying freak out is not....not good." 

"I think they'll get over it though. First dates can be pretty nerve-wracking. Plus they've clearly been dancing around each other for ages." 

"You have no idea." None too gently, Rory plopped down onto the edge of the bridge. "I've got something to ask you." 

Jess took a seat beside her and angled to look at her. "Yea?" 

"So I know that, while you're not here, and I'm not in New York, Luke's supposed to protect me. And I know you trust him. But shouldn't I learn to protect myself? Just a bit?" 

Jess was quiet a few moments before he responded. "You're right. I really should teach you some things." 

"I don't even know how to throw a punch," Rory said. She grabbed his hand. "And if I'm really gonna stick with you, and if we're really gonna be on even footing, I should at least know that."

"First, you need to learn how to make a proper fist." Jess took her hand and showed her how.

Rory nodded and paid close attention. While she hated to admit it, her safety could at some point depend on it. 

"Okay, now, bring your arm back like this." Jess guided her movements. "And then try and put all your force in it when you bring it back forward."

Rory did as he instructed. Her punch wasn't very strong but it was direct.

"Good for a first try, now, I want you to punch me. Don't even think about protesting. I need to know you can actually do some damage." 

Rory swallowed hard. Nodding, she drew back her fist and went to hit him, hesitating at the last second so that she barely tapped his arm. 

Jess frowned. "Rory. I'm wearing a leather jacket, it won't be that bad." 

"I know, I just....I don't want to be yet another person on the list of people who've hit you, whether you asked me to or not," she said quietly. 

Jess wordlessly pulled her into a hug.

Rory took in a deep breath, catching the scent of his soap, which smelled light and clean, and what she assumed was his aftershave or cologne, which smelled woodsy and warm, sort of like the brandy her grandfather liked to drink after dinner. 

"It's okay, promise. I just need to be sure should you ever need to that you can defend yourself." Jess kissed the top of her head. 

Reluctantly, Rory nodded and pulled away. Pulling her fist back once more, she let loose, putting everything she had into the hit. "Ouch," she muttered as she pulled back. Her knuckles stung from smacking against leather. 

Jess moved back a bit from the force and he moved a hand out to steady himself. "That was really good Rory." He took her hand and kissed each finger. "Better?" 

She blushed and nodded. "Yeah." Straightening up, she asked, "So?" 

"You get to pick what we do next, zip ties or knife skills."

"Which one's less physical contact?"

"Probably the zip tie, that's more of a demonstration and then I'll have you try what I showed you."

Rory nodded and said, "Then let's go with that."

Jess took out a zip tie and handed it to her he then moved his arms in front of himself, wrists pressed together. "Okay, I want you to put it around my wrists, take note of how I have my hands."

"Okay." Rory did as he asked, noting how he held his hands. "I don't even wanna know why you have a zip tie," she muttered as she checked the thing.

Jess rolled his eyes. "To teach you how to break out of them. I figured I'd have to teach you at some point how to defend and protect yourself. And plus Luke had me pick some up earlier, something about a broken shelf, so I swiped a few. Anyway, watch." Jess lifted his wrists up and tugged the zip tie as tight as it would go with his teeth. Making sure the locking mechanism was between his wrists, he then lifted his arms up over his head and brought them down as hard as he could towards his stomach, arms flaring outward. The zip tie snapped off and he was free.

Rory blinked rapidly. "Oh wow. And you want me to do that?"

Jess nodded. "It's not as difficult as it looks. By tightening the tie and then lifting your arms up and bringing them down, it puts stress on the tie at its weakest point, the locking mechanism, causing it to snap."

"Basic physics," Rory said casually. "Do we have something -- wait never mind. You've got a switchblade." Her brow furrowed a bit. "Alright let's give it a go." She held her arms out.

Jess put the tie around her wrists.

With a little bit of focus, Rory repositioned the lock between her wrists. "And here we go," she muttered.

"You can do it."

She looked at him. "Only one way to find out." With a look of concentration on her face, she pulled the tie as tight as it could go and raised her arms upwards.  
With the same force she'd put behind her punch, Rory brought her arms down and out, splitting the tie. "Yes!"

"Rory, that was great! I knew you could do it."

She smiled happily. "I'm just glad I can actually do it haha."

"There are two other methods I'm going to show you." Jess showed her how to slip out of them if her fists were pressed horizontal in the zip tie as well as how to use a knife or care to break the bar in the locking mechanism.

Rory managed to successfully complete both of the other methods, although breaking the bar of the locking mechanism presented a slight hitch. Having proven her ability to get out of a zip tie, Rory poked Jess' arm. "Alright so I beat your zip ties."

"That you did. Now, I'm gonna show you how to use this. We won't finish this lesson today, but I can at least show you a few things." Jess took out his knife.

Rory made a face. "Joy."

"Actually.... we'll use this to start." Jess picked up a stick and put the knife back. "Alright, I want you to come at me, like you plan on stabbing me, and I'm going to block and disarm you."

Rory took the stick and laughed. "Oookay."

"Hey, safety first Gilmore."

"Yeah yeah Mariano, I know." Somewhat clumsily, Rory came at him.

Jess side stepped her and then caught her wrist, stopping her as quickly as she started.

Rory froze. "Woah," she breathed.

Jess smirked and released her. "Try again.”

A determined set to her mouth, Rory backed up a step or two and tried again.

Jess used Rory's momentum against her and gently pinned her arm behind her. "And you'd drop the knife."

"Dammit," she muttered. "What am I doing wrong?"

"Rory, relax. Everyone makes these mistakes at first, it's something you have to learn and practice." Jess kissed her cheek.

"I know," she sighed, leaning into the kiss a bit. "But I want to feel like I can take care of myself. I don't want to be a damsel in distress, I wanna help you run things, hold my own!"

"And you will." Jess slid his arms around her. "Also, that reminds me. Nora Venturi is the wife of my Right Hand, George Venturi. She's offered to take you under her wing, so to speak. She wasn’t born into the life either and could teach you a few things."

Rory considered. "I'd like that. It would be nice to see where I'm headed..." She trailed off. "That is where we're headed, right?" she asked quietly.

Jess' heart sped up, not expecting that. "I..well, yes, if that's what you want."

Rory plopped down in the grass and flung herself backwards, looking upwards at the sky and trees. "I want to say yes but at the same time, 16 almost 17 seems really young...." Her voice was quiet, her tone contemplative. "Sorry if that freaked you out, it just sort of...popped out?"

"Don't apologize Rory, it's fine, just surprised me. I mean, I'd love to think that eventually the answer would be yes. But not for a few years at least." Jess laid down beside her, breathing a bit easier now.

"Guess we'll see huh?" She turned her head to look at him. "I've got a lot of faith in us."

"I do too." Jess smiled a bit. He then thought of something that made him laugh. "Lorelai would kill me, maybe you too.”

"If we decided right now that we were going to get married?" Rory asked. Laughter bubbled forth. "Oh she would. There would be another "ruining your future" lecture while she did it too."

Jess nodded in agreement.

Rory laughed a second or two longer before taking a breath and calming down. "I would like to talk to Nora," she said seriously. "I'm going to need all the help I can get keeping you in line."

Jess looked affronted. "I'm always in line!"

"Uhhhhh huh. Sure you are. You forgot to tell me that you're a legal adult, that you graduated early and therefore do not need algebra tutoring," she glared, "and you're a very bad influence. You need me to keep you on the straight and narrow."

Jess grinned sheepishly. "I really am bad at algebra through?"

Rory grinned and rolled her eyes. "Well until you're in a math class, preferably a college one so I have school bragging rights, I don't think I can help you."

"I don't think I'm going to go to college..."

"Jess," Rory said quietly. "At least give it a try? I know you don't need it but still.”

Jess sighed. "I'll think about it."

Rory grabbed his hand. “Thank you. Personally I think you’d really like it but I’ll try not to push.” Drawing his hand towards her face, she stared at his fingers as she played with his hand gently. “Besides, can’t have me outshining you can you?”

Jess smiled fondly. “I wouldn’t mind.” 

“Awh, your bullcrap is so sweet,” Rory said cheerfully. “You’d mind.”

Jess stuck his tongue out at her. 

Rory did the same and giggled. “So. I was thinking that while Mom and Luke are out tonight, we could order a pizza, maybe rent a movie?”

“Sounds good to me.”

Rory grinned. “Good. And we have to actually watch the movie because Mom will ask what we thought.”

“We will...mostly.” 

Rory blushed and swatted at him with her free hand. “Jess I’m serious,” she said with a giggle.

Jess smirked. “Mhm. We’ll see.” Jess took her hand and led them back towards town. 

As they were walking back towards Luke’s, where they would part to go help Luke and Lorelai get ready for their date, they were stopped by Lane calling out. “Jess! Rory!”

Rory and Jess stopped and let Lane catch up to them.

Lane looked at Rory. “So I heard that your mom and Luke are finally going on a date. Is it true?”

“Yea. I told Luke to get his head out of his ass and ask her out.”

Lane nodded appreciatively. “Nice. So you guys gonna help ‘em get ready?”

“Of course, Mom is already freaking out.” 

“Speaking of, I’m gonna head back to the diner, you two should catch up.” Jess gave Rory a kiss before he headed off. 

Rory grinned and grabbed Lane’s hand. “Let’s go help my mom.”

Lane laughed and followed. “So how did dinner go last night? Everyone said Jess came and spirited you away.”

“Lane, oh my god. He took me to ON20 in Hartford, and he bought me this gorgeous yellow evening gown!”

Lane smiled. “And he got you the right hair and makeup stuff right?”

“He did, and thank you!”

“It’s what best friends are for,” Lane replied matter-of-factly. “So how was ON20?”

“The food was delicious and it was so pretty! We had dinner with a journalist from GQ though.” 

Lane’s eyes widened. “What did GQ want?”

Rory grinned. “Jess landed #1 on GQ’s 30 Under 30 Business Edition. So he has a 4 page spread plus the cover photo.” 

Lane let out a breath. “Woah. That’s...woah.”

“And I’m in the spread too!” Rory blurted out in excitement. 

Lane stopped dead in her tracks. “What?”

“Yea, the Journalist took some pictures of us together and one solo shot of me! It’s on stands tomorrow.” 

Lane squealed and grabbed Rory into a hug. “Oh wow that’s amazing!!” she squealed. Calming down a bit, she asked, “So after that marvelous bit of news, tell me what happened after dinner.”

Rory blushed a bit. “We went back to his hotel room.”

“By that blush, I’m gonna guess it wasn’t just to talk and hang out.”

Rory leaned over and lowered her voice. “We had sex.” Her blush darkened but she was also smiling. 

Lane blinked rapidly. “Sex?”

“Mhmhm. And it was absolutely amazing, Lane. Oh my god. I could not have imagined it being better!” 

“Better than all the movies make it out to be?”

“So much better. And Lane. He stripped for me.” 

“Oh my God,” Lane said quietly. “He’s a keeper.”

“Mom found out though...cause uh...I got a bit liberal marking him…” Rory looked sheepish. 

“You gave him hickies?” Lane asked incredulously. “Oh my...Rory.”

Rory giggled. “Why do you think he has his collar turned up?” 

“Oh my God,” Lane groaned. “I swear.”

“You should have seen Mom’s face. She looked murderous and shell-shocked all at once.” 

“Oh I’d be willing to pay money to see that! Rory are you sure you aren’t moving too fast? I mean it’s been what, a month? Two? And you guys have already gone all the way?”

Rory frowned. “Not you too! I already had this talk with Mom. We love each other and we did it because of that. It was wonderful and the right time.” 

“Okay okay,” Lane said, holding up her hands in surrender. “That’s good and I’m happy for you. I’m just doing my job as your best friend to make sure, okay?”

Rory relaxed and nodded. 

The two resumed walking, heading towards Rory’s house to help Lorelai get ready. Lane sighed and then grinned. “I still can’t believe he stripped for you… Anyway, what’s your mom gonna wear tonight?”

“You remember that blue dress she wore to the dinner party at the Dragonfly?”

Lane nodded. “I do indeed.”

“That. We need to decide on jewelry and shoes still though...and hair and makeup.” 

“Oi,” Lane said. “We got work to do.”  
\----  
Lorelai was panicking. Ten after seven and she was looking for something, anything, to get her out of this date. “Are you sure you’re okay?” she asked Rory.

“Mom. Relax! Everything will be fine! And you look so pretty!” 

Lorelai snorted. “This is probably going to be the biggest disaster since Chernobyl,” she muttered. “What if we don’t like each other as much as we think we do? What if we run out of conversation topics? What if we--”

“MOM!” Rory yelled. “Stop freaking out! It’ll be awesome. Now shoo! He’s here.” 

The doorbell rang just then, proving Rory’s point. With a grin, Lane slipped out the back as Rory moved to open the front door.

“Hey Luke.” Rory smiled. 

“Hey, kid. Your mom ready?”

Before Rory could answer, Lorelai moved into the front hall, somewhat shy. “Hi,” she said shakily.

Rory took that as her cue to leave them be. 

“Ready to go?” Luke asked. “Oh wait. Here,” he said, offering Lorelai a bouquet of carnations.

“Oh!” Lorelai, surprised, took the bouquet and smiled. “These are wonderful, Luke. Thank you.” She set them in a vase near the door. 

Luke smiled. “You look great by the way.” He was a bit shy and it was cute. 

Lorelai blushed pink. “Thanks.” She cleared her throat. “So...shall we?”

Luke nodded and led her to his truck. He even opened the door for her. 

Still blushing like mad, Lorelai climbed in and buckled her seatbelt as Luke shut the door and ran around to get in. Jess stepped up onto the porch next to Rory and together, they waved goodbye. “Twenty bucks says they don’t come back here tonight,” Rory said mischievously.

Jess grinned. “You’re on.” 

Still grinning, Rory led Jess into the house. “So the pizza’s on the way and I picked up a movie.”

“Sounds great.” Jess led her into the living room and made himself comfortable on the couch.   
\----  
The next morning, Rory woke from her spot on the couch to the sound of a truck in the driveway. “Jess,” she mumbled, shaking his shoulder.

“Mhm?” He was mostly still asleep. 

“There’s a truck out front,” Rory said. “Not normal.”

As Jess opened his eyes the door to said truck opened and closed again. Lorelai was finally home.

Her keys rattled in the door and Rory sat up, rubbing at her eyes. “Oh man. I gotta go,” she yawned. “I have to get ready for school.”

“Kiss first.” 

“Breath stinks,” Rory muttered, dropping a kiss on his cheek. “Real kiss after I feel less nasty.”

“Fine, meet you at Luke’s.” Jess stood and stretched and headed to the door.

Lorelai finally managed to get the front door open. “Morning,” she said quietly, obvious cheer in her voice.

“Morning.” Jess half mumbled, still sleepy and continued out the front door. 

“Rory, I hope you’re getting ready to go!” Lorelai called as she moved towards the stairs.

“Almost! Give me 10 minutes!” 

“Can we make it more like five? We need to get a move on!”

“I’m trying!” Rory whined and hustled a bit faster.

Lorelai changed as quickly as she could, noting with serious annoyance the destroyed state of her hair. Grabbing a banana clip, she threw it up. “Oh, fuck it,” she muttered.

Five minutes later, Rory was ready. “MOM!” 

“Coming!!” Lorelai called as she hustled down the stairs, purse in hand. She’d managed to fix her makeup and cover the hickey on her neck but she still felt like the world knew. “Let’s go.”

Rory looked at Lorelai and then grinned. “You did dirty things, didn’t you?” 

Lorelai grabbed her arm and ushered her out the door. “What I did is none of your business.”

Rory stuck her tongue out. “Jess owes me money.” 

“How much, you little demon child?” Lorelai asked as they made their way towards Luke’s for breakfast. “And what exactly did you bet on?”

“20 bucks that you wouldn’t come home last night.” 

Lorelai groaned. “I knew that was a bad idea. But the man is more convincing than your father even.”

“Dirty!” 

“What about you? Did you break any promises last night since I didn’t return?”

“No, we just watched movies and kissed some, then we fell asleep on the couch during High Fidelity.” 

“And when you say kissing you mean a real makeout right? Please tell me you broke in the couch.”

Rory giggled. “Of course.” 

“Good. I’m proud of that in a weird way that a mother shouldn’t be, but whatever.” 

They were a few feet away from the newsstand when Rory realized why there were so many people. “Ah crap. The GQ issue is out today…” 

Lorelai looked between the crowd at the newsstand and Rory. “Well let’s go get a copy then.”

The eyes turned from the magazine to Rory when they were closer. Rory blushed. “My my, Rory, the pictures of you look stunning! And that boyfriend of yours. Mhm.” Miss Patty grinned. 

Rory blushed harder and Lorelai rolled her eyes. “Alright folks, nothing to see here. Move along. Bootsy, two copies of GQ please.”

Bootsy handed them over. 

“Thank you,” Lorelai said with a smile. Turning, she handed one to Rory. “Here you are, little one. Let’s hope there’s nothing innocence ruining,” she said jokingly.

Rory looked at the cover photo of Jess and was a bit thrown. “Damn.” It slipped out before she could stop it. 

The crowd went dead silent and everyone, even those that had been ignoring her previously, turned to look at her. “What did you just say?” Lorelai asked.

Rory’s cheeks went rosey. “Sorry! I just… look!” Rory held up the cover. Jess looked gorgeous. 

Lorelai’s eyes widened. “Curse word forgiven. Wow.”

Rory tugged Lorelai towards the diner. “I can’t even imagine what the rest look like!” 

“Guess we’ll find out,” Lorelai said as they walked in. “Where is Jess anyway?”

“Said he’d meet us at Luke’s, probably changing or something up in the apartment.” The first thing noticed was that everyone had a copy of the magazine. Rory took a seat at her and Lorelai’s favorite table and opened her magazine. 

Lorelai waved Luke over and gave him a smile as he placed her coffee in front of her. “Good morning,” she murmured.

Right at that moment Rory turned to the first spread which had a dripping wet Jess half in a pool facing another picture of him up against the Thunderbird, jeans dangerously low and shirt undone. “Holy fuck Jess…” Rory blurted out. 

Again, the crowd seemed to freeze, Taylor choked on his coffee. “Way to ruin the moment Rory,” Lorelai muttered angrily. Jess, who had walked in just as she said it, chuckled.

“What did I do now?”

“Look at this!” Rory turned the magazine around. “Sh-I mean hell, ah crap.” Rory just clamped a hand over her mouth, blushing more now. 

Lorelai gasped when she saw the pictures. “I suddenly understand why my daughter was so eager to jump in bed with you,” she murmured without thinking. Realizing what she’d said, she clapped a hand over her mouth.

“MOM!” Rory looked scandalized and Jess’ jaw had dropped. 

Luke chuckled. “Way to go, big mouth.”

Taylor was amidst a coughing fit and Babette was trying not to laugh.

“I am sooo sorry!” Lorelai said ashamedly “I honestly do not know where that came from. Would it help if I admitted to sleeping with Luke on the first date?” She clapped her hand back over her mouth.

A chorus of “LORELAI!” and “I KNEW IT!” resounded.

Lorelai looked up at Luke. “Maaaayyyybe I should take my coffee to go today? So that I don’t die of mortification before we go out tonight?”

Luke walked off to get that to go cup. Rory turned the page in the magazine to see more drop dead sexy pictures of Jess. On the last page were the ones of her and him and the solo shot of her. “Oooh…”

Lorelai looked over her shoulder. “Oh you look so gorgeous. And that dress? Perfect.”

Rory beamed. “I love that dress.” Jess came over with two cups of coffee and a chocolate muffin for Rory. 

“Thanks babe,” Rory said innocently. Grabbing her muffin and her coffee, Rory got up and grabbed Jess’ hand. “Walk me to the bus stop?”

“Of course.” Jess led the way. 

As they waited, Rory snuggled into Jess side, relishing his warmth in the chill of the spring morning. “Well that was an adventure,” she muttered.

“Up until Lorelai’s overshare it was pretty funny.” 

“Yeah I’m not sure where her filter is this morning. Possibly still on your uncle’s bedroom floor.”

Jess made a face. “Really? Was that necessary?” 

Rory shrugged. “It made me feel better. Comments on our sex lives aside, I’m glad Mom didn’t freak over the photos. Which made it to press pretty quickly. Normally it takes more like a week and half I heard.”

“They had a deadline to make, someone didn’t show so Cally had to handle the last few interviews from what I heard.” 

Rory nodded and sipped her coffee. “Makes sense. I just wish she’d put our photo together sooner, because now people are gonna be all over your pics only to get to the end and realize you have me.”

“They can drool all they want.” Jess kissed her sweetly. 

Rory grinned into the kiss and said, “I know. I just hate to break their hearts that much.” The bus pulled in. “Well that’s me. You heading back today?”  
“I am, call me when you get home?” 

“Will do!” she called as she boarded the bus. As they pulled away, Rory waved and smiled happily. God she was happy.

Jess smiled to himself and headed to his car. He’d already said bye to Luke. 

Lorelai, who was just walking out of the diner, smiled and waved at Jess. “You headed out?”

“Yea, I gotta head to work.” 

“Well, drive safe. Will we see you next weekend?”

“I will, and yes, should be back either Friday night or Saturday morning.” 

Lorelai nodded. “Good. And perhaps we can make a trip into New York?”

Jess brightened at that. “If you wanted to do that instead, that’d also work for me.” 

“Then maybe we’ll do that. I’ll let you and Rory work out the plans, yeah?”

“Sounds good.” Jess couldn’t be happier. He’d love to have Rory in New York again. 

Lorelai smiled. “Alright. Now get outta here. Go...do whatever it is you do.”

Jess laughed and got in his car. The engine roared to life and he pulled out.   
\----  
Rory stepped off the bus and walked into the courtyard area at Chilton, inwardly groaning as she noticed all the copies of GQ. 

Paris, who was tuning out Madeline and Louise’ squealing over the photos, not just of Mariano but of several others on the list, noticed as Rory stepped into the courtyard. “Luckiest girl on the planet,” she muttered.

Rory tried to ignore the attention as she made her way into the building. “Oh. My. God. She’s on the last page with him!” Madeleine squealed. 

“Whatever she’s doing, I want to know,” Louise said enviously.

Madeleine grinned. “I think it’s pretty obvious what she’s doing.”

“That Mary? Please.”

“I wouldn’t be so sure. Aria told me she saw them heading into the Hilton the other night.” 

Louise shook her head. “She’s too much of a goody goody. I’ll bet he tried and didn’t get very far at all.”

“Mhm. One way to tell, if she has any hickies, no doubt she’d be hiding them under her collar.” 

Louise nodded. “Oh definitely.”

Before they could talk about it anymore though, the bell rang calling them to homeroom and they rushed off. As the teachers moved through the announcements, Rory started to drift off, remembering curling up on the couch with Jess the night before.

“And don’t forget, ladies and gentlemen, that our annual Spring Fling is coming up in a few weeks.”

That perked Rory up. She took out her phone and shot off a text to Jess. [Oh yea, you’re gonna be my date to the Spring Fling. -R]  
She had to wait a few seconds for a reply.

[Oh really now? You’ve decided for me? -J]

Rory grinned as she read his reply. [Mhmhm. I’m sure I could convince you somehow. ;) -R]

[Well then. I guess I’ll be going. -J]

Rory’s cheeks went a bit rosey but she smirked and typed off a reply. [You shall indeed. -R]

Jess chuckled as he read that. [Love you, Booktease. Also, Lorelai suggested you guys coming to NYC next weekend instead of me coming to you. -J]

[AHHHH. Yes. <3 -R]

[Haha figured that would be your response. She’s put the plans on us so we’ll work that out this evening, yes? -J]

[Yes. :) I gotta go now, Love you, drive safe Dodger. -R]

[Will do. Love you too, Booktease. -J]

Rory grinned and stashed her phone back in her pocket just in time for the bell releasing them from homeroom.

“Look at that grin,” Louise said. “That girl knows something.”

“$50 says she was talking to her boyfriend.” 

“Stop invading her privacy,” Tristan said quietly as he joined them. “She’s got enough on her plate without worrying about you two always breathing down her neck.”

They were both surprised by Tristan’s interjection. “I...uh...right. You’re right.” Madeleine managed to reply. 

Tristan nodded and walked off, head bowed slightly. “Well that was interesting,” Louise muttered. “Someone’s carrying a torch for Gilmore…”

Madeleine nodded. “He always has though.”   
\----  
Rory walked through the front door after school that afternoon, glad she had the day off from Luke’s. “Mom?” There was no answer so Rory pulled her phone out and shot a text to Jess. [Home. Finally. -R]

Seconds later her phone was ringing. 

“Hello?”

“Hey.” Jess had just got home from work a little bit ago and was currently curled up on his bed with a book. 

“Jess!” Rory said excitedly. “Oh am I glad to hear your voice.”

“Missed you too. Good day?” 

“Well, I spent it under inspection because of course everyone knew about GQ by fourth period. But I aced my chem exam so it’s all good I guess. How was work? And when do you leave for Europe?”

“Around midnight tonight, not entirely looking forward to it. Hopefully I can get some sleep on the plane.” 

“Well you’re taking a private jet so I’d be willing to bet that you will.”

Jess shrugged. “We’ll see.” 

Rory laughed. “So New York next weekend…” she trailed off, unsure.

“Mhmhm. We could do literally whatever you want.” 

Rory thought for a second. “Will Mom be able to park in the parking garage if we drive?”

“Yea, I’ll arrange it.” 

“Okay. I’d love to say we’ll drive in on Friday night but we have dinner with my grandparents...So maybe Saturday morning?”

“That works for me.” Jess couldn’t wait. 

“Good.” Rory’s smile was audible down the line. “So you never did tell me how work went today.”

“It went good, got to leave a bit early. My friend Derek is actually going to be coming down for a bit when I get back from Europe.” 

“Oh yeah? Where from?”

“Toronto, Canada.” 

“Oh wow,” Rory said. “So how do you two know each other? Will he still be around when I get there?”

“The family business, his father is my Right Hand now.” 

“Ohh…” Rory said quietly. “And the second question?”

“I actually have no idea, I’ll have to check with him.” 

“Alright. Will he be staying at yours or hotel?”

“Mine. But if he’s still there when you arrive, he’ll move to a hotel.” 

“Well I’d hate to put him in a bind,” Rory said gently.

“He’d do the same to me if I was staying at his and Casey was coming over.” 

Rory laughed. “Okay okay. And Casey? Is that his girlfriend?”

“Yea, I tease him constantly because Casey is his stepsister. George, his father married Nora, Casey’s mom and yea.” 

Rory laughed. “Before or after Derek and Casey started dating?”

“Before.” 

“Did they know each other before hand or?”

“Nope.” 

“Wow. How do their parents deal with that I wonder?”

“They were a bit wigged at first but I mean, they aren’t actually related so…” 

“True. And what about the whole teenagers tend to be all over each other element of things?”

Jess grinned. “What about it?” 

Rory blushed. “Well, are George and Nora really strict about...you know...sex?”

“Not so much, Derek moved out so as long as it’s not under their roof…”

“Wow, that’s...that’s pretty lenient.”

Jess shrugged. “Jimmy didn’t give a fuck either way as long as I wasn’t sleeping with guys. One of his many flaws was his homophobia.” 

Rory shuddered. “And have you ever wanted to? Sleep with a guy, that is.”

Jess was quiet for a few moments. “I did once, just to see...it wasn’t bad but wasn’t for me either.” 

“Huh. I honestly did not expect that,” Rory said lightly.

“Most people never do.” 

Rory chuckled. “You’re full of surprises.”

Jess laughed. “I suppose I am.” 

Rory smiled. “Anything you want to ask me in exchange for that deep dark secret?”

Jess thought for a moment. “I’m not sure I should? I don’t want to upset you…”

“It’s only fair. I mean, I really probably shouldn’t have asked you that, but curiosity got the better of me.”

“You never mention your father…” Jess said rather quietly. 

“Oh,” Rory said gently. She shrugged. “He and my mom aren’t on the best of terms, and he’s just not really around. Everyone wanted them to get married when Mom got pregnant at sixteen and she didn’t want to and Dad’s been sort of in and out since then. Hasn’t really grown up and got himself together yet. I love him, a lot, and it’s great to see him, but he’s just not really there as much as Mom or even my grandparents are.”

“Sorry.” Jess felt a bit bad about having asked. 

“Nothing to be sorry for,” Rory said lightly. “It is what it is. I love him, and I know he loves me, I just don’t see him much and usually what he thinks doesn’t factor into stuff.”

“Ah, okay.”

“Yeah...I’m sure he’ll call if he sees the GQ spread but I wouldn’t count on it otherwise.”

Jess nodded. “Probability that he will hate me?” 

Rory considered. “Based on the photos? Maybe seventy percent. Interview? Twenty. Combined? Maybe a good eighty five?”

“Ah. To be expected.” 

“Basically. But then again, everyone’s dad hates their kid’s significant other, right?”

“True.” 

“I mean, I’m pretty sure Jimmy wouldn’t have liked me had we met.”

Jess tensed. “Jimmy was a dickbag.” 

“...He knew about me didn’t he?”

“Briefly…” 

“Well, he got what was coming to him.”

Jess smiled a bit at that. “Yea, he did.” 

“So now that we’ve shared our deep dark secret for the week, what shall we discuss?” Rory asked brightly, changing the subject.

“How about how much The Fountainhead sucks.” 

“Hmm...nope. Considering it is my favorite book, that you offered to read.”

Jess grumbled. “I’m a third of the way through and it’s killing me.” 

Rory laughed. “Well since I’m talking to you and you sound just fine, I’m gonna go with that’s an exaggeration and tell you to grow up.”

“Of course I sound fine now I’m not currently reading it.” 

“Jess,” Rory said, amused. “You’ll survive. If I could survive Hemingway, you can survive this.”

“Fine.” Jess huffed. “Only cause I love you.” 

“I know,” Rory said sweetly. “And I’ve got you wrapped around my little finger.” She was clearly joking but it was still so obviously true she had to giggle.

Jess rolled his eyes but smiled. 

“So what’re you up to? Got everything ready for you to go tonight?”

“I was reading before our call, pretty much plan on doing that till I have to leave and yea, I have everything packed.” 

“Good. And you’re sure you have everything?” Rory was very much determined to take care of him.

“Positive. I checked twice.”

She nodded, despite knowing he couldn’t see her. “Good. What were you reading?”

“I Slept with Joey Ramone by Mickey Leigh.” 

“That sounds…interesting?”

“You’d like it.”

“Maybe I’ll borrow it, then. Since you are reading The Fountainhead for me.”

“I’ll be sure to leave some good notes in the margins for you then.” 

Rory grinned. “I’d like that. I still haven’t looked at your notes in Howl yet, though.”

“Rory, you’ve had that for ages now! That’s your homework, before you come to New York.” 

“And if I don’t?” she asked playfully.

“Might just have to punish you,” Jess teased. 

“Maybe I’d rather have the punishment.” There was laughter evident in her tone.

Jess smirked. “Huh. Well then, it’s up to you.” 

Rory laughed. “Any idea what the punishment would be? So I can make a fully informed decision,” she said cooly.

“I think there’s a conversation we need to have before this goes any further.” 

“And that would be? This is new territory for me.”

“Honestly for me too. Most of my experience is from quick fucks, nothing kinky really at all…only read about that side of things.” 

Rory felt herself blush. “This is already nerve wracking,” she said quietly. “Not in a bad way necessarily, just something new and difficult.”

Jess paused for a moment. “I vote you do some research, I further mine and we talk about this Saturday.” 

“I like that plan,” Rory said, relief clear in her voice.

Jess grinned when he said his next piece. “I also vote we have sex a few more times before we get into the other stuff.” 

Rory’s breath hitched and she felt her cheeks heat up, knowing they must be bright red. “You are so lucky my mom is not home,” she said, slightly breathless. “And if I cursed, I would have some choice words for you right now.”

Jess laughed a bit before catching his breath to speak again. When he did, he made sure it had a rough edge to it. “Just for the record, my bedroom is soundproof…”

“You little shit,” Rory hissed. She muttered something about needing those damn pills already before clearing her throat and saying, in as serious a voice as she could muster, “Well then maybe I’ll just sleep on the couch.”

“I’ll be sure to wear only a pair of boxers and get up for many a glass of water then.” 

“And I’ll just sleep with my back to the kitchen and hallway. And I’ll wear my old fashioned button down pajamas.”

“Then I’ll just zig zag my way back to my room, after all it’ll be dark, I could get lost.” Jess then grinned. 

Rory laughed. “Oh yeah sure. I know you navigate that place in the dark plenty well. And that’s a pretty big assumption you’re making there, thinking you’re guaranteed the chance to undress me.”

“I’d be content to watch you undress yourself too.” 

Rory made a quiet noise of distress. Trying to not sound like that made her incredibly hot, she said, “Again, assuming something you shouldn’t, Mariano.”

“Of course, I’d also be more than happy to put on a show for you if that was more your thing.” 

Rory groaned. “Jess….you make it really hard to be a good girl.”

“Where’s the fun in that? And if you get lonely between now and Saturday, you can always turn to page 32 in GQ.” 

“What?” Rory was taken aback. “Are you suggesting what I think you’re suggesting?”

“Depends, what do you think I’m suggesting.” The smirk was evident in his voice. 

Rory went to give a smart retort and the words stuck in her throat. Clearing her throat, she tried again. Since her wit was obviously failing her, she flat out said, “It sounds like you’re suggesting I masturbate to those way-too-hot pictures of you that I would rather not have allowed the world to see.”

“That’s exactly what I’m suggesting. Also, thank you for the compliments, much appreciated.” 

Her breath was gone. “Jess…”

“Rory.” Jess’ voice was bordering on husky. “I can tell you I was definitely thinking of you during that photo shoot.” 

She gasped. “Oh my God.”

“ROOOOOOOORY, MOMMY IS HOME!” 

“Oh crap,” Rory muttered. “I gotta go. JUST A SECOND MOM!”

“Alright, and...Sweet dreams, Rory.” Jess hung up before she could respond. 

Lorelai came into the kitchen and poked her head into Rory’s room, taking note of the obvious flush in her cheeks and the phone in her slightly shaky hand. “Jess?”

Rory nodded, blush darkening against her wishes.

“I’m not gonna ask. Instead, I am going to ask how your day was.”

“It was pretty good, everyone and their uncle had a copy of GQ.” 

Lorelai nodded. “Everyone at the Inn had it too. But besides that?”

“The Spring Fling is coming up, Jess is going to go with me. And we talked about New York.” 

“Ahhh the Spring Fling. I’m assuming you need a dress? And what was the final decision on plans?”

“I do. Maybe we could go looking for one this weekend? And we’ll drive in Saturday morning, Jess will have a space for us in the garage and we’ll stay with him.” 

“Sure, as long as Jess doesn’t mind us taking the time to do that. And sounds good. He has guest rooms right?”

“Yep, his place is huge from the pictures I’ve seen.” 

Lorelai nodded and turned to head back into the kitchen. “You have work?”

“Not today, Luke has a shipment coming in so he closed early.” 

“And is he coming with us?”

“Luke? I have no idea. Shouldn’t you? You’re dating him.” 

Lorelai sighed and started the coffee pot. 

“Mom? Did something happen with you and Luke?” 

“What? Oh, no...we just...we haven’t really talked since this morning. I didn’t have the guts to stop by the diner earlier.”

“MOM! You need to go over there and talk to him! But before you do, I need you to do something for me.” 

“I know okay? I just...ugh. And what do you need?”

Rory blushed a pretty shade of red. “I really need to get birth control before Saturday...” 

Lorelai froze. “Oh God. Um…” She thought for a second. “Oh! Let me call the doctor’s office and see if they can squeeze us in, since you don’t have to work.”

“Thank you!” She called after Lorelai. 

“Uh huh,” Lorelai called back as she grabbed the phone and dialed the doctor’s office. There were quiet murmurs for a minute or so and then Lorelai popped her head back through Rory’s door. “Let’s go!”

Rory grabbed her phone and a coat and followed Lorelai to the jeep. 

As they drove into Hartford, Lorelai fidgeted anxiously. Not only was she taking her daughter for birth control of all things, but she knew she was putting off the conversation she had to have with Luke.

Rory was smiling down at her phone. [Headed to the Dr’s -R]

[-attachment- -J] It was a picture of a sadface drawn in the margins of The Fountainhead.

Rory laughed. [The reading will pay off. -R]

[If you say so. -J]

[You know why I’m going to the Dr right? -R]

[Yes, Rory, I kind of put it together. I really got you hot, didn’t expect you to go as soon as you hung up. -J] Jess teased.

[Making sure. And honestly I wasn’t expecting to either. But this was when we could get in. Otherwise no sexy times for you. -R]

[Thank god for impromptu appointments then. -J]

[Figured you’d say that lol. -R]

[:P -J]

[:P to you too. -R]

Rory hadn’t even noticed the car had stopped moving, too focused on her texting with Jess.

“Earth to planet Rory! We’re here,” Lorelai said. “Let’s go!”

“Oh! Right.” Rory blushed and stashed her phone in her pocket.  
\----  
When Rory was called back, Lorelai stayed in the waiting room, fiddling with her phone. She knew she should call Luke -- they needed to talk -- but she was unexplainably nervous. This conversation could make or break their relationship before it even began. Deciding it was better to know, she flipped open the phone and dialed him before she could chicken out.

“Hello?” 

“Luke? It’s Lorelai.”

“Oh! Lorelai, hey. How are you?”

“Well, I’m sitting here waiting for Rory to get out of the exam room with a prescription for birth control, so I’m sort of trying not to lose it. You?”

“Oh man…” Luke didn’t even want to think of that. “I’m pretty good, busy, but good. Just got a shipment of stuff in.

“Oh well then I won’t keep you but...Well we need to talk about us.”

“Well, we could have dinner when you get back? I should be done putting everything away by then.”

“O-okay,” Lorelai said. Her hand was shaky. 

“Lorelai? Try to relax.” Luke said good naturedly. 

“Me? Pssssht. I’m as relaxed as they come.”

“Uh huh. Sure. Well, I’ll put on coffee anyway. Just this once though.” 

“Luke, I…” Lorelai bit her lip. “Thanks. I don’t know why this freaks me out so much. Once we get out of here, I’ll drop Rory at home and stop by the diner.”

“Sounds good, see you then.” Luke hung up with a smile. 

Lorelai closed her phone and released a breath she hadn’t realized she was holding. He’d seemed happy to hear from her so maybe everything was going to be okay…

A few minutes later, Rory skipped out from the back, a grin on her face. “Alright. All you have to do is pay and then drop this,” she said, brandishing a prescription, “at the pharmacy.”

Lorelai was startled. “That was fast.”

Rory smiled brightly. “Mhmhm.” 

“Alrighty then. Let’s go. I bit the bullet and called Luke. I’m supposed to meet him at the diner afterwhile for dinner.”

“Yay! Have fun.” Rory had almost said ‘don’t do anything I wouldn’t do’ but somehow she figured that wouldn’t be funny to Lorelai. 

Lorelai rolled her eyes and dragged Rory to the desk so they could pay out. “Sure.”

They were on the road in mere minutes. [Mission complete. -R]

[ ;) -J]

After dropping the prescription at the pharmacy with a promise to pick it up in an hour, Lorelai dropped Rory at home before heading to Luke’s.  
Luke was in the middle of cooking for him and Lorelai. 

As she pushed open the door, the bell jingled and she startled. As empty as the place was, the sound travelled oddly.

“Lorelai?” Luke came out from the kitchen. 

“Hi,” she said weakly.

Luke smiled, “Food will be ready in a few minutes.” He set a cup of coffee in front of her. 

With a nod, Lorelai sat down and latched onto the cup, needing something familiar in what was uncharted territory.  
As he’d promised, he brought the food out a few minutes later. 

Lorelai swallowed hard. “It looks great.”

Luke sat down beside her. “You should say whatever is on your mind or it will be nagging at you all the way through the meal.” 

“Where do we stand? Like as a couple. Are we a couple? Are we dating? What are we?”

Luke responded calmly. “I was under the impression that it was a combination of dating and being a couple.” 

Lorelai let out a slow breath, trying to calm down. “But what does that mean? Does it mean that I can invite you to New York with me and Rory without it being weird? Are we doing the whole “going steady” thing where we don’t see other people? Because those are things that I’d like but at the same time am absolutely terrified of.”

“I..w-well...sure I’d like to go to New York with you.” He hadn’t been expecting that and took a few seconds to process it before he spoke again. “I’d like us to ‘go steady’ as you put it. But what exactly are you terrified of?” 

Lorelai looked down into her coffee. “I’m not...great at long term relationships. And what if...what if we do this and it ends badly and then I can’t face you enough to even come in here to get coffee? What if we make Rory and Jess feel awkward and it starts to drive a wedge in between them and us? What if I can’t...what if I can’t do this?” she asked quietly. “I’m absolutely terrified that I will wreck whatever we have without wanting or trying to.”

Luke placed his hands on her shoulders. “Lorelai, take a deep breath, maybe a few of them.” 

Lorelai nodded and sucked in a deep breath before letting it out and drawing another.

“One, I’m not sure anyone is good with long term relationships, they’re something you work at. Two, Rory and Jess will be fine, they set us up in the first place. Three, I think you’ve got yourself so worked up you’re freaking yourself out and me a little bit to be honest. I don’t think you’ll mess anything up, you just need to calm down. We’ve done pretty great so far.” 

Lorelai nodded and took another deep breath. “I just...I really want this...us...to work and I’m scared that I don’t know how to do that.” She looked up at him. “I don’t want to sabotage myself but I’m worried I will out of habit more than anything else.”

Gently, Luke took the coffee cup from her hands and placed it on the counter before taking her hands in his own. “Lorelai, just take it as it comes. And if you think you’re gonna sabotage yourself, just talk to me, okay? Relationships take work and are based on communication. I have to know that you understand you can come to me. I’m here for you.”

Lorelai blinked rapidly. “You mean that?”

“Of course I do. Now come on, let’s eat before it gets cold.” Luke, much as he cared for Lorelai, could only take so much emotional talk in one go.

Lorelai laughed. “Okay, then.”  
\----  
“Richard!” Emily stormed into his study and slammed a copy of GQ onto his desk. “I can’t believe it! That...that boy! And Lorelai is letting her! Argh!” 

Richard peered at the cover through his reading glasses. “It’s a nice photo,” he murmured.

“Turn to page 32 and 33.” Emily grit out. 

Richard, wary of the way his wife’s jaw was tensing, opened the magazine to the pages she’d indicated. Within seconds, his jaw managed to both tense and drop at the same time. “Good Lord.”

“Exactly! Just look at that...that display! Now, turn the page.” 

Richard did and gasped in shock. “Who in the world let her outside in that dress?!” He looked closer. “And this pose is entirely inappropriate for a national magazine!”

“I’m well aware Richard! And wait ‘til you read the interview!” 

Richard squinched his eyes shut and pinched the bridge of his nose. “I’m not entirely sure that would be a good idea for my health.”

“Fine, it gets worse though! They had dinner at ON20 and Bitty Hendricks saw them enter the Hilton together!” 

“Emily, she isn’t Lorelai,” Richard finally said. “It is entirely possible they just went to the Hilton to spend time together, since I’m going to assume the boy was staying there.”

Emily sighed, frustrated. “Did you know he secured a contract with the Euro 5?” 

“I do vaguely recall hearing something to that effect, but only just. Good on him. At least he can take care of Rory.”

Emily still wasn’t pleased. “He was emancipated at age 15.” 

Richard sighed heavily. “So he’s legally an adult. Do you seriously think that will change how Lorelai or Rory feel about him? He’s laid claim to her, remember, and unless she backs out, that’s it. There’s no keeping him away from her, not without risk of personal damage. I’ve done some asking around and he’s a good kid. Has an upstanding reputation and a good business sense. And he is very loyal.”

“Fine, then I want to meet him. We’ll ask Rory at dinner Friday.”  
\----  
Lorelai and Rory were both desperate to be anywhere other than Emily and Richard’s come Friday evening. Rory was nervous they were going to grill her about GQ; Lorelai was panicked they would somehow have heard about Luke. 

“Can we just go?” Rory asked quietly.

Lorelai stuck her tongue out and rang the doorbell.

Emily answered the door. “Lorelai. Rory,” she said cordially.

“Hi Grandma.” Rory smiled and stepped inside. 

Lorelai followed her. “Hi Mom. Something smells good.”

Emily led them into the living room. “I should hope so, we hired a new cook.” Richard came in to join them as well. 

“What’s that, the third one this year?” Lorelai asked as she and Rory sat down.

Emily made a sour expression at her before she went to make their drinks. “Lorelai, Rory.” Richard greeted them, newspaper in hand. 

“Hi Dad.”

“Hi Grandpa. How’re you?”

“Wonderful, and you?” He took a seat beside Lorelai.

“I’m great. Mom and I are going to New York tomorrow.”

“Oh?” Emily piped in, trying to keep a neutral expression. 

“Yes,” Lorelai said. “We’re going dress shopping for the Spring Fling and are going to see Jess along with his uncle Luke.”

“Hmm. Well where will you be staying?” Emily sipped at her drink. 

“Jess invited us to stay with him,” Rory said innocently.

Emily forced down an unpleasant reaction. “Oh.” She set her glass down and walked swiftly to the dining room. “Dinner is ready, come along,” she stated briskly.   
Lorelai and Rory shared a look before they got up and followed.

“What’s eating her?” Lorelai whispered to Richard.

“Probably the GQ issue featuring our granddaughter,” he replied just as briskly and followed Emily into the dining room. 

Lorelai shook her head and blinked a bit before making her way into the dining room and taking a seat.

Rory was feeling the chill; dinner wasn’t looking good. She followed Lorelai into the dining room and took her seat. 

As they started dinner, Rory surreptitiously looked around the table. Her grandparents seemed stiff and unwelcoming. Her mother looked edgy, and somewhat ashamed. Her parents disapproval never failed to affect her, despite years of experience with it.

Rory quietly ate her meal, not quite sure what to say. 

“So, Rory,” Emily finally said, dabbing at her mouth with her napkin. “Your grandfather and I would very much like to meet the young man you’re seeing. Especially after you appeared with him in that...charming,” the word came from between gritted teeth, “GQ spread.”

Rory flashed Lorelai a discreet panicked look. “O-okay,” Rory stuttered out. 

“We’ll see which Fridays he might be free and let you know,” Lorelai said firmly, stepping in for her clearly distressed child. “The boy has a company to run after all.”

Richard nodded his approval. “Good.” 

“Now that that’s dealt with, can we please please defrost the evening? I’m starting to get freezer burn,” Lorelai quipped.

Emily shot her a displeased look but complied. “Fine.” 

Lorelai tipped her head in thanks and took a sip of her drink. God she could use some alcohol.

The rest of the dinner seemed to go by with ease; but Rory still couldn’t wait to get home. 

As the evening drew to a close, Lorelai and Rory seemed to pull closer and closer together until finally they were pressed together side by side as Emily showed them out.

“We’ll see you next week. Have a wonderful time in the city.” Rory appreciated her grandma at least trying to go through the motions.

Once they were in the car and on their way, Rory relaxed. "That was very stressful." 

“What is an Obvious Statement, Alek?” Lorelai quipped. “Let’s just be thankful that it’s over.”

Rory nodded. "Just wait til she finds out about Luke."

Lorelai groaned. “Yes because that is definitely something I want to have happen.”

Rory stuck her tongue out. "I had to deal with it. You will too at some point."

As they rolled into Stars Hollow later, Lorelai grinned. “Speaking of Luke, shall we stop for coffee?”

"Yes please!" 

Laughing gently, Lorelai parked the jeep on the street in front of the diner and hopped out, locking the doors before they headed inside. “Hey got time to give us coffee?”

Luke made made a face. "You and your coffee addiction." He walked over and put in a new pot.

“You love me for it,” Lorelai teased as she sat down at the counter. “Plus, we just survived the most hellish dinner with my parents yet.”

Luke looked sympathetic. "I take it they saw the GQ issue?"

“Saw it, bought it, read it, wanna meet him,” Rory muttered darkly into her coffee.

"Good luck." He patted her head. 

“Thanks,” she grumbled. “But at least we get to see him tomorrow.”

Luke smiled. "I hear his place is really nice."

“All the pictures look stunning,” Lorelai said.

“I researched the building and it’s amazing!” Rory added. “Lounges, pool, all sorts of nice amenities.”

"Wow." Lorelai was impressed, Luke too.

“Yeah. So I think there’ll be no shortage of things to do while we’re in the city.”

Rory was so excited. "Oh, I think Jess' best friend will be in town too." 

Luke and Lorelai shared a look. “In town? From where?”

"Toronto, Canada." 

Luke nodded appreciatively and Lorelai choked a little on her coffee. “His best friend is coming in from Toronto? Does he play hockey?”

Rory shrugged. "He might? His name is Derek Venturi." 

Luke gave her a look that said she better stop there, and Lorelai seemed placated with Rory’s uncertainty.

Rory focused on her coffee after that. A few minutes later she stood, "I'm going to head home.   
"Have fun."

Rory trudged her way home, feeling weighed down by both her experience at dinner and her excitement for the next morning, which couldn’t come fast enough.


	11. I'm A Keeper

**Summary for the Chapter:**

> Rory, Luke and Lorelai arrive in New York, where they get to meet someone very special to Jess.

**Notes for the Chapter:**

> Before you murder us, we're sorry! We got very busy and while we intended to get this posted a couple of weeks ago, some things got in the way. So here we go with chapter 11, the first of two going up today!

Rory yawned as they drove through the city towards Jess’ apartment, nursing a cup of coffee she’d gotten when they stopped for gas and bathrooms. Luke and Lorelai were, as per usual, bickering slightly in the front seat but in such a sappy way it almost hurt to listen to.  
“Turn here,” Rory spoke up. “It’s that fancy building a few blocks away.” Rory pointed.  
“It’s almost like you’ve been here before,” Lorelai joked as she followed Rory’s directive.  
Rory stifled her panic. “I looked it up online.” Moments later they were pulling in the garage; their spot was next to Jess’ Thunderbird.  
“And we’re here!” Lorelai said in a singsong tone. “Told you I’d get us here safely,” she said, poking Luke in the ribs.  
“Yeah we’re here after two near crashes and an angry shouting match.”  
Rory got out and pretended to look at the map. “This way.” She led them to the elevator that had penthouse access. Inside, Rory punched in the code Jess gave her.  
“Wow,” Lorelai said under her breath as the elevator shot upwards. They were deposited in the hallway outside Jess’ door and Rory skipped over to ring the bell.  
Jess opened it in mere moments. “Hey.” He smiled, happy as could be.  
“Jess!” Rory squealed, throwing herself into his arms.  
Lorelai laughed “Careful, munchkin.”  
Jess laughed and caught her and spun her around. “Missed you too.” Jess then set her down and moved aside to let Luke and Lorelai inside. Luke’s jaw dropped.  
“The pictures do not do this place justice,” he said reverently.  
Jess smiled sheepishly. “You can set your bags down for now, and I can give you the tour?”  
The trio nodded and dropped their bags just out of the way and then followed Jess for a tour, Rory holding his hand tightly the whole time.  
“This is the great room: Kitchen is there, pantries are off to the side, you’re in the foyer obviously, dining room, living room and then the hallway leads off to the other rooms. There is a balcony off the living room behind the middle curtain panel.”  
Lorelai whistled under her breath. “Wow. I...just wow.”  
Jess led them down the hallway next. He pointed out the guest bath, two guest rooms, library, office, and lastly his bedroom.  
“So what are the sleeping arrangements?” Lorelai asked coolly.  
“Well I haven’t figured that out. I have two guest rooms but I wasn’t sure if you and Luke would be sharing?”  
The two shared a look and then turned away to have a quick murmured conversation. “We’re sharing,” Luke said firmly.  
“Then uh..” Jess looked a bit nervous, with a slight blush. “Rory can have the other guest room or share mine…”  
Rory turned to face Lorelai, back to Jess and made puppy eyes at her.  
“You’ve got the pills, you’re smart and I’m here so you get to make the choice yourself,” Lorelai said, calmly.  
Rory blushed but finally spoke up. “I’ll share with Jess.” Jess did well at hiding his excitement.  
Lorelai squinched her eyes shut for a moment and squeezed Luke’s hand. “Okay. Well, why don’t we all take some time to settle in and then maybe we can hit the shops? Or the park? Or food? Or all three.”  
“All three sounds good. We could pick up some food and eat in the park?” Jess piped up.  
There was a general agreement and then they all drifted back to get their bags and move them to rooms. Rory, who was moving slower that Luke and Lorelai, could hear their murmured conversation as she passed by but didn’t stop to listen. For all she knew, it could be a conversation that was rapidly turning intimate.  
Jess picked up Rory’s bag and carried it into his room and shut the door. He’d cleared a portion of his bookcase for her as well as space in his closet.  
“Are you expecting me to move in?” she asked lightly.  
Jess rolled his eyes then smiled. “No, but you should feel like you have your own space.”  
“Awh babe,” she said, smiling as she wrapped her arms around his neck.  
Jess smiled down at her and kissed her sweetly.  
Grinning, Rory said, “I missed you a lot.”  
“Missed you too, Booktease.”  
“And those pictures? Not close enough to the real thing at all.”  
Jess’ grin turned into a smirk. “Oh?”  
“Mhm. Definitely not close enough.”  
“We’ll have to fix that then.”  
Rory giggled and said, “I think we have a conversation to have first.”  
Jess smiled. “Later. Let’s get you unpacked first, Lorelai will want food soon.”  
Rory laughed, a full, complete laugh. “You already know her so well!”  
Jess smiled and set her bag on the bed. “Have at it.”  
Rory squealed slightly and did just that, unpacking in record time before zooming back to Jess and hugging him. “Thank you.”  
Jess kissed her cheek. “You’re welcome.”  
“Think we have a few minutes?”  
“I think so. What do you have in mind?”  
She pulled his face to hers and kissed him. “Just talking.”  
“Mhmkay.” Jess kissed her again, a bit more needy.  
Rory groaned. “Okay bad idea. New topic.” She kissed his neck.  
“Like?” Jess failed at biting back a moan.  
“How I can get you to make that sound again.”  
“I think you know,” Jess replied, breathily.  
“I do,” Rory said knowingly. “But I was wondering if I could make you say it.” She admitted the last bit shyly.  
Jess blushed. “Well...a number of things..like...that thing you just did.”  
Rory went to say something but before she could, Lorelai’s voice carried down the hall. “You kids ready?”  
‘Uh, yea! Coming!” Rory gave Jess one last kiss before leading him out.  
“That was hot...Mistress,” Jess whispered in her ear as they moved towards the door.  
“Come on!” Luke hollered.  
Rory felt a tingle go down her spine and rose colored her cheeks. She rather liked being called Mistress. It was...pretty freakin hot.  
She blinked and tried to school her expression. “You are sooo going to pay for that, boy.”  
“I should hope so.” Jess smirked.  
“Count on it.”  
They finally went to go meet Lorelai and Luke.  
Lorelai looked them over. “Still dressed, still unrumpled, alright. Where to first?”  
“Food!”  
Laughing lightly, Lorelai shook her head. “Alright then.”  
They headed a few blocks away to one of Jess’ favorite delis. It was Italian owned of course. “Ah! Jess!” An elderly Italian woman hugged Jess.  
Jess smiled. “Mrs. Alessi.”  
The old woman smiled and looked him over. “You look tired.” She caught sight of Rory. “And who is this?”  
“This is my girlfriend Rory, my uncle Luke and Rory’s mother Lorelai.”  
“Oh!” she exclaimed. “This is the girl from the magazine, yes?” She pulled Rory into a hug. “Oh it is nice to finally meet the girl who makes Jess so happy.”  
Jess blushed a bit. “Ah, yea. That’s her.”  
Mrs. Alessi smiled and patted Rory’s cheek. “Friends and family discount for you, eh? And your mother.”  
Rory blushed and smiled shyly. “Thank you.”  
“You’re very welcome. Jess where have you been?”  
“Been jet setting around the world on business.”  
“Ahh, and not eating right, either.” She tutted. “Take care of yourself.”  
Jess smiled and kissed her cheek. “I will, try not to worry.”  
Mrs. Alessi shook her head and threw up her hands in exasperation but smiled lovingly. “I will always worry, child. Always. So I know you aren’t just here for talk. You need to eat.”  
She showed them to one of the few booths and gave them all menus.  
Rory looked over the menu. “I can’t decide.”  
“The Bella Vita is really good.” It had grilled chicken, prosciutto, mozzarella, red onion and tomato, along with an italian dressing of sorts.  
Rory considered. “I’ll try that then.”  
Jess ordered the same.  
Lorelai settled for a muffaletta and Luke got a salad.  
They all chattered away as Mrs. Alessi made their food.  
“So where shall we head after this?” Lorelai asked. “I figure today is probably our best bet for shopping for a dress, but what stores do we wanna hit when?”  
“You could always try 5th Avenue and I’d definitely try SoHo and Tribecca. Maybe even Dumbo.” Jess pointed out.  
“Kid knows his stuff,” Lorelai said. “Rory?”  
“But..those places are so expensive?”  
Jess leveled her with a look. “Rory. I can more than cover it.”  
“Jess. You aren’t supposed to buy my dress.”  
“I’m not. Technically she is.” He all but tossed Lorelai his card.  
Rory huffed in frustration. “Okay correction. You aren’t supposed to pay for my dress.”  
“Too bad.” Jess grinned.  
Rory whined and looked at Lorelai. “Mom!”  
“Kid, he’s offering to buy you a designer dress, on par with all those other rich kids at school. Let him.”  
Rory grumbled but agreed. Mrs. Alessi came out with their food -- she even threw in homemade chips.  
Stomachs growling, the group dug in, all enjoying it immensely. The dress conversation was dropped but Rory wasn’t prepared to let it go quite yet.  
Jess smiled. He’d missed eating here. Mrs. Alessi was like family to him. “Mrs. Alessi, you should come join us.”  
The old woman grinned. “As much as I would like to, someone has to run the deli.”  
Jess tsked. “And you say I work too much. Ten minutes won’t hurt.”  
“Ah next time. Ten minutes with you tends to become more like two hours.”  
“Fine, fine. Then at least let me give you this. Picked it up in London.” He reached into his pocket and pulled out a pretty Rose pendant with gold chain.  
Mrs. Alessi gasped. “Oh you spoil me child. I couldn’t possibly.”  
“You can and you will. You practically raised me.”  
She got misty eyed at that. “Caro bel bambino di nonna…” Jess stood up and she hugged him tight.  
Lorelai looked at Rory. “What did she say?” she asked quietly.  
Rory had no idea but she was smiling at the scene. Jess could be really sweet. Luke spoke up, “Roughly, my dear beautiful grandson or grandchild. My Italian is basic at best.”  
Lorelai smiled. “Awh.”  
Jess helped Mrs. Alessi put the necklace on.  
“Oh, sweet child,” Mrs. Alessi said. “You are too good to me.”  
Jess smiled. “Never. You deserve the best.”  
She smiled and patted his cheek. “And so do you. But I think you’ve found her,” she said conspiratorially.  
Jess’s cheeks went a bit red, but he agreed.  
Rory smiled and ducked her head as she ate a bit of sandwich. It was nice seeing Jess so open and unguarded with someone else.  
Jess excused himself to the bathroom and Mrs. Alessi took that chance to take out a few old pictures. They were of little tiny Jess. “When I first met my sweet Jess, his English was very poor.” She smiled at the memory.  
Rory tilted her head a bit but Lorelai beat her to it. “Like...not his first language poor or small child poor?”  
“Jess’ first language was Italian. When we met he could hardly get out the words to ask for an apple.”  
“Oh wow,” Lorelai said quietly. “I never would have guessed.”  
“I would have,” Rory said. “He resorts to Italian when he’s flustered.”  
Mrs. Alessi laughed. “That he does. Also when angry. I helped him learn though, Spanish too. His father was no good. Didn’t care much about making Jess be in school.”  
Lorelai pursed her lips and Luke muttered something rude under his breath.  
“Jess was such a sweet boy though. Always helped me around the shop. Very bright.” She beamed. “He loved going to the library, I helped him get a card. He’d have so many books in his pack he’d nearly tip over!”  
Rory giggled. “Sounds like him!”  
She flipped through a few more pictures, and then...there was one of little Jess with a cast on his arm and Mrs. Alessi’s smile faltered.  
Rory caught notice and took the old woman’s hand. “Jimmy’s handiwork?”  
She sighed sadly and nodded. “I hadn’t seen him for a few days and he comes in...broken. It hurt my heart.”  
Luke placed a gentle hand on her arm. “I know the feeling.”  
She smiled, grateful for their kind words and comfort. “I have some of his awards on display.” She gestured to the wall across from them. Various school awards were framed and hung. A few poems and drawings too. One noticeably had a small stick person next to a lady stick person. It had childlike handwriting, in Italian of course.  
Rory grinned when she noticed. “What does that one say?”  
“It says: Happy birthday, love Jess. He tried to make me a cake but...uh.. you can imagine how that turned out.” She laughed.  
Rory’s grin widened. “Oh I can. Are you the one that taught him to cook?”  
“I am! He is a natural, learned very quickly.”  
Jess had been back for a while, but was content to lurk in the back and listen to Mrs. Alessi reminisce; it was sweet and she deserved it. It also meant she was taking a much needed break.  
Rory caught Jess’ eye and smiled. She was loving hearing about his childhood. He decided then was as good a time as any to reveal himself. “I had a great teacher.”  
Mrs. Alessi startled a bit but blushed gently. “Oh, you know you don’t need to flatter me.”  
“I only speak the truth, Nonna.”  
She smiled and rolled her eyes. “Yes and my tears are strong enough to cut diamond.”  
Jess laughed and murmured something to her in Italian.  
Lorelai sat there quietly, in a state of shock. Jess was so different around this small Italian woman. Luke, slightly less shocked, took Lorelai’s hand and gave it a squeeze.  
Eventually, Mrs. Alessi got back to work and the foursome finished eating. Jess went up to the register to pay and of course, tipped generously.  
The old lady grinned and shook her head. “That is far too much.”  
Jess grinned. “It’s hardly enough.” He made a donation to the Parish box as well.  
“That’s my boy,” the woman murmured. “Now go, spend some time with that lovely girl of yours.”  
“Yes, Nonna.” He gave her another hug before they headed out.  
Rory grinned and caught his hand as they walked. “She’s precious. And you were too cute.”  
Jess blushed and smiled shyly. “She’s great.”  
“It was nice to see you so happy and open. And to hear about your childhood.”  
Lorelai smiled. “She’s very sweet. Very proud of you.”  
Jess was a bit surprised by Lorelai’s words but smiled. "That she is."  
Luke grinned. “I’m glad someone’s been taking care of you. And she seems like a tough little old lady.”  
Jess grinned. "She threatened Jimmy with a meat cleaver when I was seven."  
Luke whistled, obviously impressed. “Tough.”  
Rory grinned and wrapped an arm around Jess’ waist as they walked. “I’m glad she looked after you,” she said quietly.  
Jess kissed her cheek in response. He was glad to have had Mrs. Alessi too.

**Notes for the Chapter:**

> Hope you enjoyed this! I'm sorry you guys have been waiting for son long but we really do appreciate you guys sticking with the story.


	12. If You Can Afford Me

**Summary for the Chapter:**

> Jess takes Rory shopping for an outfit for the Spring Fling.

**Notes for the Chapter:**

> As promised, a second chapter today!

For a while, they walked, window shopping, until Rory spotted something she wanted to try on. In several shops, Rory tried on only one dress, just to make a face, or have it vetoed by the whole group. It wasn’t until they walked into Chanel and Rory spotted a little black dress that made her gasp that there seemed to be any end of the shopping excursion in sight.  
Luke and Jess were sitting in the lounge area of the store with drinks. Lorelai walked up behind Rory. "Found the one?"  
Rory nodded. “I think so. Excuse me,” she said to the shop assistant. “Can I get that one in a size seven?”  
The woman smiled and headed off to the back to get one.  
When she returned, the dress draped over her arms, Rory followed her to a dressing room and, giddily, pulled the dress on, zipping it shut and turning this way and that as she looked in the mirror.  
Lorelai waited impatiently for her to come out. "Hurry up! Mommy is excited!"  
Giggling, Rory stepped out of her dressing room and looked at Lorelai. “Oh this is so it.” The dress, with it’s sweetheart neckline and cap sleeves, was fitted and showed off Rory’s curves, stopping a few inches above the knee.  
Rory grinned. "Think he'll like it?"  
Lorelai smiled. “He’s crazy if he doesn’t. Go show him.”  
Rory shook her head. "No, I want it to be a surprise."  
Laughing Lorelai shook her head. “You are going to kill him, girl. Guess that means it’s staying in my room tonight huh?”  
Rory nodded, beaming. "I'm going to go change now." She all but skipped back to the dressing room.  
Lorelai, smiling, went back out to the waiting area. “We have a dress!”  
"Isn't she coming out?" Jess looked confused.  
“She wants to surprise you,” Lorelai said, her smile sharpening to a grin. “But it looks amazing on her.”  
Jess pouted. "Okay... well, as long as she's happy."  
“She is,” Lorelai said happily. “So we’re gonna go wrap this up and then I figured we might split up for dinner? I figured you’d want her to yourself for a bit, maybe try to talk her into some shoes or jewelry?”  
Jess grinned. "Exactly."  
Lorelai smiled and shook her head. “Good luck. She’s already against you paying for the dress.” With that, Lorelai stepped away to go pay for the dress with Jess’ card.  
Rory came out a few minutes later and went over to Jess, happy as could be. “Thank you for the dress, Mr. Mariano,” she said softly, sitting in his lap.  
Jess slid his arms around her. "You're welcome. I hear you look stunning in it."  
She leaned against him, head on his shoulder. “I do. Don’t know what I’m gonna wear with it, but it looks great so.”  
"Come on then, let's go. I'm taking you to dinner and Luke is taking Lorelai." He didn't mention anything about shoes or jewelry yet. Food first.  
Rory looked at her mom. “Ooh la la. Guess we’ll see you later then.”  
Lorelai stuck her tongue out.  
Rory replied in kind and, giggling, got up and pulled Jess with her. “Let’s go then.”  
Jess led her out and hailed a taxi. He was taking her to a french bistro in SoHo.  
“And where are we going?” Rory asked as they sped off.  
"Bistro Les Amis."  
“Ooooh French. Sounds delightful.”  
“It’s good, I’ve been a few times.”  
Rory smiled and looked out the window to watch the city pass by, eyes big with wonder. “This place is amazing,” she said quietly.  
The cab pulled up and let them out in front of the bistro; Jess paid the fare. “I stumbled on this place walking back from Washington Square Park one day.”  
Rory grinned. “Looks like the sort of place you’d frequent.”  
“Their food is phenomenal.”  
“Can’t wait to try it then!”  
Jess held the door open for her and the hostess led them to their table, recognizing Jess.  
Rory smiled, looking around as she sat down. “Wow. It’s...wow.” Expectantly, she looked up at the hostess, ready to take her menu.  
Jess smiled and took the single menu from her; he ordered a nice bottle of wine as well as ice waters for them.  
As the hostess walked away, Rory looked at Jess. “Um...are we sharing a menu?”  
“No, I’m going to read it to you.”  
Rory sighed. “Jess, I do know how to read.”  
“Oh, so you can read French?”  
Rory blanched a little but straightened. “Probably enough to get by.”  
Jess glanced at the menu and selected something at random. “Le boeuf avec ratatouille aubergine, radis, èpinards, et courgettes.” He glanced up and waited for her to translate.  
Rory sat for a second and muttered to herself. “Umm...beef with ratatouille something, radish, something and something.”  
Jess laughed. “See? You need me.”  
Sticking out her tongue, Rory asked, “So what is it?”  
“Aubergine is eggplant, èpinards is spinach, and courgettes are zucchinis.”  
“Well at least I knew it was beef.”  
Jess laughed again. “Well, what are you in the mood for? Chicken, duck, beef, pork, lamb, seafood?”  
Rory thought for a second. “Ummm...chicken.”  
“In a pasta or as itself?”  
“In a pasta!”  
Jess read off the names and descriptions of a the dishes that fit the criteria.  
Rory picked one and grinned. “I’m a sucker for a good fettucine.”  
Jess motioned the waitress over and gave her his and Rory’s orders in flawless French. Impressed, Rory took a sip of her water. “Wow.”  
Jess smirked. “I take it my French skills impress you?” He poured the wine.  
She nodded. “Considering my French consists of bare minimum, survival vocabulary and a lot of grammar.”  
“I could always teach you.”  
“I’d much rather you teach me Italian.”  
Jess was a bit surprised. “I...wow...yea. I’d love to.”  
Rory tilted her head. “You okay?”  
“I just wasn’t expecting that.”  
“It’s your first language. Why wouldn’t I want to learn at least a little?”  
Jess didn’t really have a response.  
“Plus, it’s really annoying to have to stop and ask you for translations when you let it slip in bed,” she said quietly, placing her hand over his on the table.  
Jess grinned. “We’ll start with that then.”  
Rory giggled.  
Their waiter came by with rolls and butter.  
“So why is Italian your first language anyway?”  
“Jimmy never spoke English around me and anyone he had take care of me from infancy up until I was like five spoke only Italian.”  
“Oh wow,” Rory said quietly. “That’s...it’s like he was setting you up for failure.”  
Jess nodded, fist clenched.  
Rory grimaced. “I wish you’d let me take a whack at him,” she muttered darkly.  
“You can always spit on his grave.”  
Rory shrugged. “Lacks oomph but I’ll take what I can get,” she said with a grin.  
Jess reached across the table to take her hand.  
Rory gave his hand a squeeze. “What?”  
“Nothing, just felt like holding your hand.”  
Rory grinned. “Oh okay. So. After dinner, where we headed? I seriously doubt you took me to an early dinner just to take me back to your place after.”  
“Not at all. We’ve tickets to see Les Miserables.”  
Rory’s eyes went wide. “Really?!”  
“Mhmhm. Front row, in the orchestra.”  
Rory squealed. “Oh my God. This is one time I will totally not object to being treated very very well.”  
Jess grinned.  
Rory looked wary for a second. “That grin...you have something up your sleeve.”  
“Nope. Drink your wine.”  
Rory made a face. “I don’t know why you ordered me any, I barely touch it.”  
“This one has low alcohol content and it’s sweeter.”  
“It’s not that I just don’t drink it.” Rory shrugged. “I’ll give it a try but I probably won’t drink even half the glass.”  
Jess shrugged.  
Rory rolled her eyes and took a sip. “There, happy? It’s good, just not my thing.”  
Jess shrugged again. “To each their own.”  
Taking another sip of the wine, Rory sighed. “I just don’t want you to spend a lot of money on wine I’ll barely touch.”  
“Rory, relax. Money isn’t important.”  
“Jess, I know you’ve got a lot, but that doesn’t mean waste it. And buying me wine I won’t drink is a waste.” Their food arrived just then and Rory held her thought while the waitress placed the food on the table before asking for some more ice water.  
The waitress nodded and she went off to get the pitcher.  
“If you wanna spend money on me, buy me things I will actually consume. Like books.”  
“Or I can keep ordering you wine and use that as an excuse for me to have two glasses,” he teased.  
The waitress came back and Rory smiled, murmuring a thank you as she poured more water in her glass. “Or I can drink my glass just to spite you and make you buy yourself a second glass.”  
Jess pouted.  
Rory grinned. “Besides, only prostitutes have two glasses of wine with a meal.”  
“Well then drive me to Reno because I am open for business,” Jess said in mock seriousness.  
Rory started cracking up. “Oh my God.”  
Jess pointedly took a sip of his wine.  
With a roll of her eyes, Rory took a sip of her water and then went to try her pasta. “Ohh that is so good.”  
Jess smiled. “Glad you like it.”  
Rory took a sip of her wine then. “And it goes with the damn wine.”  
Jess grinned. “I’m well aware.”  
Rory stuck her tongue out and then really dug into her dinner. “Wanna try a bite?” she offered.  
Jess nodded and opened his mouth.  
Gently, Rory gathered a bite and fed it to Jess. “Pretty sure you’re gonna have to figure out how to make this for me.”  
“I already know how, Gilmore.” Jess grinned and dug into his own food.  
“Of course you do,” Rory muttered good naturedly.  
Jess smirked.  
As they ate, they talked about various things until Jess started trying to find out things about her Spring Fling dress. “I’m not telling you,” Rory said in a sing song tone.  
“Rory!” Jess whined.  
Rory grinned. “The best kind of prize is a surprise.”  
Jess sighed. “Fine.”  
Rory giggled and pulled apart a roll. “I will tell you that it’s black though. Just so you can pick a suit.”  
Jess sighed. “Thanks.”  
“You’re welcome, babe.” Rory grinned proudly.  
Jess offered her a bite of his food.  
Rory leaned forward and accepted it. “Oh wow that’s good. What is that?”  
“Terrine de Canard Maison au Poivre Vert or homemade duck terrine with green peppercorn & pink salt.”  
“Yum. Never had duck before. You know how to make this too?” she teased.  
Jess nodded. “Duck’s pretty easy to cook. You can eat it rare like you can beef.”  
Rory raised an eyebrow. “Maybe you can but I like my meat to not come to my plate making noise.”  
Jess rolled his eyes. “There is a big difference between rare and raw.”  
“I know that Jess. I just don’t care for my meat rare. I’m more of a medium to medium well gal.”  
“As long as you don’t eat it well done. That’s blasphemous.”  
“Oh I agree with you there.”  
Jess smiled. “Will you want dessert?” Jess was almost finished with his meal.  
“Split something with me?” Rory asked sweetly.  
“Sure.”  
With a big smile, Rory asked, “Creme brulee?”  
“I’ll order it.” Jess smiled.  
Rory squealed quietly and smiled happily.  
It arrived a few minutes later.  
Grabbing a spoon, Rory scooped up a bite and offered it to Jess. “Open.”  
Jess did so and waited for the bite.  
Rory went to feed it to him but, with a giggle, pulled it away and ate it herself, laughing at his shocked expression.  
Jess pouted. “Rory!”  
"Ohh come here, poor thing." She scooped up another bite and fed it to him. "Better?"  
Jess happily ate the bite. “Yes.”  
Rory smiled. "Good. Because otherwise it would make the coming conversation difficult."  
Jess blinked, confused.  
"Well we still have to have that kink talk," Rory said quietly. "And you don't talk when you're grouchy."  
Jess was glad he hadn't taken a drink yet, he probably would have spit it out. "Right."  
Rory giggled. "We can wait if you want."  
"Nope, we'll do it later tonight."  
"After Les Mis?"  
"Yea." Jess took another spoonful of the creme brulee.  
Rory nodded. "Okay. So....yeah. Are we going to the show right after this?"  
"Not exactly." The conversation paused as Jess paid the cheque.  
"Are we going back to your place for a bit?"  
"Actually, I thought you'd want to get some shoes and maybe some jewelry to go with your dress..." Jess guided her out to a taxi.  
For a minute, Rory was quiet. "Jess, you...babe you shouldn't. You already paid for my dress and that was expensive."  
"I want to. Rory, I'm not hurting for money. Let me do this, okay?"  
"I just...this is one of those things where I can't reciprocate and that just sort of...bugs me?"  
Jess resumed conversation once they were in the cab. "Rory I don't need you to buy me things. I'm happy just to have you around. And you seemed pretty excited about this dance when you asked me, I just want to help make it as special as possible."  
"I know you don't need me to but I want to. I want to do something to make you feel special or make something special for you. This dance is special because you're going. The dress and the shoes and the jewelry and all that don't matter."  
"You want to do something? Read Hemingway and let me spoil you."  
Rory leaned her head on his shoulder. "Time to pay the piper for The Fountainhead huh? And I'm trying. It's just....not normal for me."  
Jess leaned over and gave her a kiss in response. A few minutes later they pulled up outside of Tiffany's.  
Eyes huge, Rory gasped quietly. "Um...Jess. You..."  
“Come on.” Jess paid the cabby and helped Rory out of the cab. “You okay?”  
Rory nodded. "I um....just sort of...Kinda never thought I'd be stopping here with the intention of going in."  
“How jealous will Lorelai be?” Jess led her to the entrance.  
"Umm...well not very since she's been here but yeah."  
“Try and relax, okay?’ Jess led her inside.  
"Yeah I'll try but...I feel like Audrey Hepburn."  
“You’re far prettier than Audrey.” Jess whispered to her.  
Rory blushed scarlet. "T-thanks. I..."  
“Let’s take a look at the bracelets?” Jess grinned and led her over to a jewelry case.  
"Okay." Rory, as much as she hated to admit it, was pretty excited to look at shiny baubles.  
Front and center in the jewelry case was the iconic sterling silver heart charm bracelet.  
"Jess, can I...?" she asked shyly, her hand at her mouth like she was going to bite her nail. "I've always wanted one."  
“Of course. You can get it engraved too.” Jess smiled and asked the attendant if they could see the bracelet.  
Rory smiled very shyly and grabbed Jess' hand. "But what would I even have it say?"  
“They tend to only like to keep it at initials or monograms.”  
Rory nodded and blushed a little bit. "Makes sense." She thought for a second. "RG JM. Would that work you think?"  
Jess checked with the attendant who said it was more than okay.  
Rory smiled. "I'd like that, please."  
Jess told the man they were going to continue shopping as well and led Rory over to the necklace case.  
"Oh I was just gonna wear the locket," Rory said genuinely as they made their way over.  
“Just look anyway? Might see something else you like.”  
"Okay," she said softly. For a while, she looked over the pieces behind the glass, thinking them pretty but not right for the dance. At one point, she stopped and pointed at a piece and muttered, "Birthday or Christmas," and then kept moving.  
Jess watched her as she looked, taking note of the ones she made comments about.  
All of a sudden, she stopped and pointed. "That." At the end of her finger was a stunningly simple but gorgeous rose gold arrow embedded with small round diamonds.  
Jess asked to see it and the attendant took it out. “Ah, lovely selection from our Hearts collection, 18K rose gold with gorgeous diamonds. Chain is 16’’ long.”  
Jess glanced at Rory, “We’ll take it.” Jess also had an idea just how expensive it was too.  
Unable to hold back anymore, Rory squealed and threw her arms around Jess. "Thank you."  
Jess laughed and held her close. He kissed her properly and passionately when the attendant walked away.  
She felt dizzy, and slightly like this couldn't be real. Normal girls from small Connecticut towns did not end up falling in love with billionaire businessteens.  
Unbeknownst to Rory or Jess, paparazzi saw the two enter and had gotten quite a few shots of the pair in Tiffany’s & Co.  
Rory looked up at Jess, slightly breathless. "Please tell me shoes will be slightly less overwhelming."  
Jess smiled. “A little. Lorelai instructed me to take you somewhere that had both Louboutins and Jimmy Choos...so…”  
Rory gasped and danced with glee. "My favorites."  
Jess laughed and led her out to the curb. He’d already helped her on with her bracelet and necklace.

**Notes for the Chapter:**

> Hope you enjoyed!

**Author's Note:**

> Updates soon to follow! Thanks for reading!


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